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890707-28-5

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890707-28-5 Usage

Description

Bardoxolone is a synthetic oleanane triterpenoid with multifunctional activities in the control of cellular growth and differentiation. It is capable of activating the transcription factor peroxisome proliferator activator receptor-γ (PPARγ) and exhibits apoptotic effects in malignant cells independently of PPARγ. Bardoxolone is an off-white powder and has been developed as a potential drug for the improvement of hyperglycemia, proteinuria, glomerulus structure, and serum creatine, which may be beneficial in treating diabetic kidney diseases, cancer, and thromboembolic events.

Uses

Used in Pharmaceutical Industry:
Bardoxolone is used as a potential drug for the treatment of diabetic kidney diseases, cancer, and thromboembolic events. Its multifunctional activities in controlling cellular growth and differentiation, along with its ability to activate PPARγ and induce apoptosis in malignant cells, make it a promising candidate for these applications.
Used in Diabetes Management:
Bardoxolone is used as an agent for improving hyperglycemia, proteinuria, glomerulus structure, and serum creatine levels in patients with diabetic kidney diseases. Its potential to regulate these parameters may contribute to better management and treatment outcomes for diabetes-related complications.
Used in Cancer Therapy:
Bardoxolone is used as an anticancer agent, targeting malignant cells and inducing apoptosis independently of PPARγ. Its multifunctional activities in controlling cellular growth and differentiation make it a promising candidate for cancer treatment, potentially offering a new approach to managing this disease.
Used in Thromboembolic Event Prevention:
Bardoxolone is used as a preventive agent for thromboembolic events. Its potential to improve serum creatine levels and other related parameters may contribute to reducing the risk of thromboembolic complications in at-risk patients.

Check Digit Verification of cas no

The CAS Registry Mumber 890707-28-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,9,0,7,0 and 7 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 890707-28:
(8*8)+(7*9)+(6*0)+(5*7)+(4*0)+(3*7)+(2*2)+(1*8)=195
195 % 10 = 5
So 890707-28-5 is a valid CAS Registry Number.

890707-28-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Amino-5-chloro-N,3-dimethylbenzamide

1.2 Other means of identification

Product number -
Other names 2-amino-5-chloro-N,3-dimethyl-benzamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:890707-28-5 SDS

890707-28-5Synthetic route

2-amino-3-methyl-5-chlorobenzoic acid methyl ester
79101-83-0

2-amino-3-methyl-5-chlorobenzoic acid methyl ester

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In methanol at 65 - 68℃; for 5h; Temperature;98%
In methanol at 45℃; for 6h;97.2%
In ethylene glycol; acetonitrile at 0 - 70℃; for 17.5 - 23h; Product distribution / selectivity;84.8%
isopropyl 2-amino-5-chloro-3-methylbenzoate

isopropyl 2-amino-5-chloro-3-methylbenzoate

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In isopropyl alcohol at 60℃; for 7h;96.8%
2-amino-5-chloro-3-methylbenzoic acid ethyl ester

2-amino-5-chloro-3-methylbenzoic acid ethyl ester

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In methanol at 50℃; for 6h;95.4%
6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione
120374-68-7

6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
With acetic acid In ethyl acetate at 35 - 45℃; for 0.333333h;95%
With acetic acid In ethyl acetate at 22 - 52℃; for 0.333333 - 2.75h; Product distribution / selectivity;93%
With acetic acid In water; acetonitrile at 25 - 30℃; for 2.5h; Product distribution / selectivity;87%
6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione
120374-68-7

6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

methylamine hydrochloride
593-51-1

methylamine hydrochloride

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
With potassium hydrogencarbonate In acetonitrile at 25 - 30℃; for 3h; Solvent; Reagent/catalyst; Temperature;93.6%
Stage #1: methylamine hydrochloride With triethylamine In dichloromethane at 20℃; for 2h;
Stage #2: 6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione With acetic acid In dichloromethane; ethyl acetate Reflux;
With potassium carbonate In ethanol at 25 - 80℃; for 5.5h; Reagent/catalyst; Temperature;
2-amino-5-chloro-3-methylbenzoic acid
20776-67-4

2-amino-5-chloro-3-methylbenzoic acid

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2h;
Stage #2: methylamine In dichloromethane at 0℃; for 2h; Temperature;
92.6%
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With thionyl chloride for 3h; Reflux;
Stage #2: methylamine In tetrahydrofuran; water at 20℃; Cooling with ice;
59.3%
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With thionyl chloride for 3h; Reflux;
Stage #2: methylamine In tetrahydrofuran; water at 20℃; for 12h; Cooling with ice;
59.3%
6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione
120374-68-7

6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

methylamine
74-89-5

methylamine

A

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

B

6-chloro-3,8-dimethyl-2,4(1H,3H)-quinazolinedione

6-chloro-3,8-dimethyl-2,4(1H,3H)-quinazolinedione

C

2-amino-5-chloro-3-methylbenzoic acid
20776-67-4

2-amino-5-chloro-3-methylbenzoic acid

Conditions
ConditionsYield
With water; acetic acid In ethyl acetate at 48 - 52℃; for 1h; Product distribution / selectivity;A 87.3%
B 3.4%
C 1.7%
N-methyl-3-methyl-2-aminobenzamide
870997-57-2

N-methyl-3-methyl-2-aminobenzamide

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide; acetic acid at 5 - 20℃;85%
Stage #1: N-methyl-3-methyl-2-aminobenzamide With hydrogenchloride In N,N-dimethyl-formamide at 10 - 30℃;
Stage #2: With sodium sulfite In water; N,N-dimethyl-formamide at 30 - 35℃; for 3.25h;
Stage #3: With sodium hydroxide; sodium sulfite In water; N,N-dimethyl-formamide at 10℃; for 0.25h; pH=2.2; Product distribution / selectivity;
72.7%
With N-chloro-succinimide In acetonitrile for 1h; Reflux;
With sulfuryl dichloride In dichloromethane at 0 - 30℃;
With thionyl chloride In acetonitrile at 40 - 50℃;
carbon monoxide
201230-82-2

carbon monoxide

2-bromo-4-chloro-6-methylphenylamine
146948-68-7

2-bromo-4-chloro-6-methylphenylamine

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
palladium diacetate; 1,4-di(diphenylphosphino)-butane In ethylene glycol at 25 - 110℃; under 2842.59 Torr; Inert atmosphere; Sealed tube;70%
2-amino-5-chloro-3-methylbenzoyl chloride

2-amino-5-chloro-3-methylbenzoyl chloride

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
In dichloromethane
In dichloromethane
2-amino-5-chloro-3-methylbenzoic acid
20776-67-4

2-amino-5-chloro-3-methylbenzoic acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / Reflux
2: dichloromethane
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / Reflux
2: dichloromethane
View Scheme
Multi-step reaction with 2 steps
1.1: 1,4-dioxane / 2 h / 50 °C
2.1: triethylamine / dichloromethane / 2 h / 20 °C
2.2: Reflux
View Scheme
2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate
1391132-23-2

2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate

2-(dimethylamino)ethyl 2-amino-5-chloro-3-methylbenzoate
1391132-24-3

2-(dimethylamino)ethyl 2-amino-5-chloro-3-methylbenzoate

methylamine
74-89-5

methylamine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
at 110℃; under 3876.26 Torr; for 6.06667h; Product distribution / selectivity; Sealed tube; Inert atmosphere;
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
2.1: thionyl chloride / 3 h / Reflux
2.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
2.1: thionyl chloride / 3 h / Reflux
2.2: 12 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / Cooling with ice
2: N-chloro-succinimide / acetonitrile / 1 h / Reflux
View Scheme
o-toluidine
95-53-4

o-toluidine

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium sulfate / water / 40 °C
1.2: Reflux
2.1: sulfuric acid / 0.33 h / 80 °C
3.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C
4.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
5.1: thionyl chloride / 3 h / Reflux
5.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1.1: sodium sulfate / water / 40 °C
1.2: 0.17 h / Reflux
2.1: sulfuric acid / 60 - 80 °C
3.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
3.2: pH 4
4.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
5.1: thionyl chloride / 3 h / Reflux
5.2: 12 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1.1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 0.17 h / Reflux
2.1: sulfuric acid / 0.83 h / 70 - 80 °C
3.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
4.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
5.1: thionyl chloride / 3 h / Reflux
5.2: 12 h / 20 °C / Cooling with ice
View Scheme
2-(hydroxyimino)-N-(2-methylphenyl)acetamide
1132-03-2

2-(hydroxyimino)-N-(2-methylphenyl)acetamide

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sulfuric acid / 0.33 h / 80 °C
2.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C
3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
4.1: thionyl chloride / 3 h / Reflux
4.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: sulfuric acid / 60 - 80 °C
2.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
2.2: pH 4
3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
4.1: thionyl chloride / 3 h / Reflux
4.2: 12 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: sulfuric acid / 0.83 h / 70 - 80 °C
2.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
4.1: thionyl chloride / 3 h / Reflux
4.2: 12 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid / 1,2-dichloro-ethane / 12 h / 0 - 30 °C
2.1: acetic acid; dihydrogen peroxide / 0.25 h / 5 °C
2.2: 28.17 h / 5 - 20 °C
2.3: 3.75 h / 10 - 40 °C
3.1: acetic acid / ethyl acetate / 3.25 h / 0 - 25 °C / pH 9 - 10
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid / 1,2-dichloro-ethane / 12 h / 0 - 30 °C
2.1: acetic acid; dihydrogen peroxide / 0.25 h / 5 °C
2.2: 28.17 h / 5 - 20 °C
2.3: 3.75 h / 10 - 40 °C
3.1: potassium carbonate / ethanol / 5.5 h / 25 - 80 °C
View Scheme
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C
2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
3.1: thionyl chloride / 3 h / Reflux
3.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
1.2: pH 4
2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
3.1: thionyl chloride / 3 h / Reflux
3.2: 12 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C
3.1: thionyl chloride / 3 h / Reflux
3.2: 12 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid; dihydrogen peroxide / 0.25 h / 5 °C
1.2: 28.17 h / 5 - 20 °C
1.3: 3.75 h / 10 - 40 °C
2.1: acetic acid / ethyl acetate / 3.25 h / 0 - 25 °C / pH 9 - 10
View Scheme
Multi-step reaction with 3 steps
1: sulfuryl dichloride; acetic acid / 120 - 125 °C
2: sulfuric acid; acetic acid; dihydrogen peroxide / 60 - 65 °C
3: ethyl acetate / 20 °C
View Scheme
benzoic acid
65-85-0

benzoic acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetic acid; chlorine / 3 h / 30 - 40 °C / Inert atmosphere
2.1: 0.08 h
2.2: Grignard reagent / 1 h
3.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C
4.1: zinc; sodium hydroxide / 2 h / 70 °C
5.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C
5.2: 2 h / 0 °C
View Scheme
3,5-dichlorobenzoic acid
51-36-5

3,5-dichlorobenzoic acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 0.08 h
1.2: Grignard reagent / 1 h
2.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C
3.1: zinc; sodium hydroxide / 2 h / 70 °C
4.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C
4.2: 2 h / 0 °C
View Scheme
3-Chloro-5-Methylbenzoic Acid
56961-33-2

3-Chloro-5-Methylbenzoic Acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C
2.1: zinc; sodium hydroxide / 2 h / 70 °C
3.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C
3.2: 2 h / 0 °C
View Scheme
toluene
108-88-3

toluene

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: oxygen; cobalt(II) aceylacetonate; N-hydroxyphthalimide / dichloromethane / 1 h / 30 °C / 22502.3 Torr / Sealed tube
2.1: acetic acid; chlorine / 3 h / 30 - 40 °C / Inert atmosphere
3.1: 0.08 h
3.2: Grignard reagent / 1 h
4.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C
5.1: zinc; sodium hydroxide / 2 h / 70 °C
6.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C
6.2: 2 h / 0 °C
View Scheme
2-methyl-4,6-dichloroaniline
30273-00-8

2-methyl-4,6-dichloroaniline

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: copper bromide / N,N-dimethyl-formamide / 18 h / 90 - 95 °C
2: sodium hydroxide / 10 h / 70 - 75 °C
3: sulfuric acid / 16 h / Reflux
4: methanol / 5 h / 65 - 68 °C
View Scheme
2-amino-5-chloro-3-methylbenzonitrile
939990-03-1

2-amino-5-chloro-3-methylbenzonitrile

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / 10 h / 70 - 75 °C
2: sulfuric acid / 16 h / Reflux
3: methanol / 5 h / 65 - 68 °C
View Scheme
3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen / ethanol / 4 h / 50 °C / 1500.15 Torr
2: chlorine / 1,2-dichloro-ethane / 3 h / 50 °C
3: sulfuric acid / 6 h / 5 °C / Reflux
4: isopropyl alcohol / 7 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogen / ethanol / 4 h / 50 °C / 1500.15 Torr
2: chlorine / 1,2-dichloro-ethane / 3 h / 50 °C
3: sulfuric acid / 6 h / 5 °C / Reflux
4: methanol / 6 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogen / ethanol / 4 h / 50 °C / 1500.15 Torr
2: chlorine / 1,2-dichloro-ethane / 3 h / 50 °C
3: sulfuric acid / 8 h / 5 °C / Reflux
4: methanol / 6 h / 45 °C
View Scheme
Multi-step reaction with 3 steps
1.1: thionyl chloride / toluene / 90 - 100 °C
1.2: 0 - 10 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol
3.1: acetic acid; hydrogenchloride; dihydrogen peroxide / 5 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: pyrographite; hydrazine hydrate; sodium hydroxide; iron(III) chloride hexahydrate / water / 70 °C
2: pyridine / acetonitrile / 4 h / 50 - 60 °C
3: acetic acid / water; acetonitrile / 1 h / Reflux
4: thionyl chloride / acetonitrile / 40 - 50 °C
View Scheme
m-Toluic acid
99-04-7

m-Toluic acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: nitric acid / -10 - -5 °C
2.1: thionyl chloride / toluene / 90 - 100 °C
2.2: 0 - 10 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol
4.1: acetic acid; hydrogenchloride; dihydrogen peroxide / 5 - 20 °C
View Scheme
N,3-dimethyl-2-nitrobenzamide
600126-70-3

N,3-dimethyl-2-nitrobenzamide

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / methanol
2: acetic acid; hydrogenchloride; dihydrogen peroxide / 5 - 20 °C
View Scheme
6-methylisatoic anhydride
66176-17-8

6-methylisatoic anhydride

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / water; acetonitrile / 1 h / Reflux
2: thionyl chloride / acetonitrile / 40 - 50 °C
View Scheme
5-chloro-7-methyl-1H-indole-2,3-dione
14389-06-1

5-chloro-7-methyl-1H-indole-2,3-dione

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; acetic acid; dihydrogen peroxide / 60 - 65 °C
2: ethyl acetate / 20 °C
View Scheme
(E)-2-(hydroxyimino)-N-(o-tolyl)acetamide

(E)-2-(hydroxyimino)-N-(o-tolyl)acetamide

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / 60 - 65 °C
2: sulfuryl dichloride; acetic acid; dihydrogen peroxide / 60 - 125 °C
3: ethyl acetate / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: sulfuric acid / 60 - 65 °C
2: sulfuryl dichloride; acetic acid / 120 - 125 °C
3: sulfuric acid; acetic acid; dihydrogen peroxide / 60 - 65 °C
4: ethyl acetate / 20 °C
View Scheme
3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid
500011-86-9

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

rynaxypyr
500008-45-7

rynaxypyr

Conditions
ConditionsYield
With 3-Methylpyridine; methanesulfonyl chloride In propiononitrile at -5 - 20℃; for 4h; Product distribution / selectivity;97%
With 3-Methylpyridine; methanesulfonyl chloride In acetone at -5 - 5℃; for 3h; Product distribution / selectivity;96.4%
With pyridine; methanesulfonyl chloride In acetonitrile at -5 - 20℃; for 4h; Product distribution / selectivity;96.8%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

C9H6Br2ClN3O2

C9H6Br2ClN3O2

C18H15Br2Cl2N5O2

C18H15Br2Cl2N5O2

Conditions
ConditionsYield
With pyridine; methanesulfonyl chloride In acetonitrile at -5℃; for 2.16h;95.6%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

acetone
67-64-1

acetone

6-chloro-2,2,3,8-tetramethyl-2,3-dihydroquinazolin-4(1H)-one
1488427-93-5

6-chloro-2,2,3,8-tetramethyl-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 1h; Reflux;95%
furfural
98-01-1

furfural

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

6-chloro-2-(furan-2-yl)-3,8-dimethyl-2,3-dihydroquinazolin-4(1H)-one
1542270-67-6

6-chloro-2-(furan-2-yl)-3,8-dimethyl-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With β-cyclodextrine-SO3H In water at 50℃; for 0.416667h; Green chemistry;94%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxaldehyde
1072138-63-6

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxaldehyde

C18H14BrCl2N5O
1351217-99-6

C18H14BrCl2N5O

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 1h; Reflux;92%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride
943982-60-3

3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride

rynaxypyr
500008-45-7

rynaxypyr

Conditions
ConditionsYield
Stage #1: 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine With 3-Methylpyridine In acetonitrile at 25 - 35℃;
Stage #2: 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride In acetonitrile at 25 - 35℃; Solvent; Temperature;
91.1%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; Cooling with ice;89.3%
Stage #1: 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine; 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride In acetonitrile at 20℃; for 1.16667h; Reflux;
Stage #2: With sodium hydrogencarbonate In acetonitrile Product distribution / selectivity;
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

cyclohexanone
108-94-1

cyclohexanone

6'-chloro-3',8'-dimethyl-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one
1542270-66-5

6'-chloro-3',8'-dimethyl-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one

Conditions
ConditionsYield
With β-cyclodextrine-SO3H In water at 50℃; for 0.416667h; Green chemistry;90%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carbonyl chloride

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carbonyl chloride

rynaxypyr
500008-45-7

rynaxypyr

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3.16667h; Reflux;84%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

dicyanozinc
557-21-1

dicyanozinc

2-amino-3-methyl-5-cyanobenzoyl-N-methylamine

2-amino-3-methyl-5-cyanobenzoyl-N-methylamine

Conditions
ConditionsYield
With zinc; bis(tri-tert-butylphosphine)palladium(0) In 1,4-dioxane for 11h; Product distribution / selectivity; Heating / reflux;83%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

potassium cyanide
151-50-8

potassium cyanide

2-amino-3-methyl-5-cyanobenzoyl-N-methylamine

2-amino-3-methyl-5-cyanobenzoyl-N-methylamine

Conditions
ConditionsYield
chloro(1-naphthyl)bis(triphenylphosphine)nickel(II); chloro(2-naphthalenyl)bis(triphenylphosphine)nickel In ethanol; xylene at 45℃; Product distribution / selectivity;82.5%
With zinc; bis(tri-tert-butylphosphine)palladium(0); 18-crown-6 ether In 1,4-dioxane for 24h; Product distribution / selectivity; Heating / reflux;65%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

C9H6ClN3O
1450664-91-1

C9H6ClN3O

6-chloro-2-(3-chloro-1-(pyridin-2-yl)-1H-pyrazol-5-yl)-3-cyclopropyl-8-methyl-2,3-dihydroquinazolin-4(1H)-one
1450664-92-2

6-chloro-2-(3-chloro-1-(pyridin-2-yl)-1H-pyrazol-5-yl)-3-cyclopropyl-8-methyl-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 1h; Reflux;82%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

C19H13Cl3F3N5O2
1104384-03-3

C19H13Cl3F3N5O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;81%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

1-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carbonyl chloride
1104384-31-7

1-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carbonyl chloride

C21H16Cl3N5O3
1104384-07-7

C21H16Cl3N5O3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;81%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

C8H3Cl3N4O

C8H3Cl3N4O

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-chloro-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-chloro-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In acetonitrile76%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

1-(6-chloropyrazin-2-yl)-3-bromo-1H-pyrazole-5-carbonyl chloride

1-(6-chloropyrazin-2-yl)-3-bromo-1H-pyrazole-5-carbonyl chloride

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In acetonitrile75%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

C12H7Cl2F2N3O2

C12H7Cl2F2N3O2

N5-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-4,5-difluorophenyl)-N3-methyl-1H-pyrazole-3,5-dicarboxamide

N5-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-4,5-difluorophenyl)-N3-methyl-1H-pyrazole-3,5-dicarboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;75%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

C12H7Cl2F3N2O2

C12H7Cl2F3N2O2

N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-5-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-5-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;73.5%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

5-chloro-2-(2-chloroacetamido)-N,3-dimethylbenzamide
1374598-54-5

5-chloro-2-(2-chloroacetamido)-N,3-dimethylbenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3.6h;73%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

C10H3BrCl2F2N2O

C10H3BrCl2F2N2O

3-bromo-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-4,5-difluorophenyl)-1H-pyrazole-5-carboxamide

3-bromo-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-4,5-difluorophenyl)-1H-pyrazole-5-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;73%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

1-(pyrazin-2-yl)-3-bromo-1H-pyrazole-5-formyl chloride

1-(pyrazin-2-yl)-3-bromo-1H-pyrazole-5-formyl chloride

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(pyrazin-2-yl)-1H-pyrazole-5-carboxamide

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(pyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In acetonitrile72%
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine
890707-28-5

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

C9H6Cl2N4O2

C9H6Cl2N4O2

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-methoxyl-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-methoxyl-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In acetonitrile71%

890707-28-5Relevant articles and documents

A PROCESS FOR THE SYNTHESIS OF ANTHRANILIC ACID/AMIDE COMPOUNDS AND INTERMEDIATES THEREOF

-

, (2022/04/03)

The present invention disclosed a process for the synthesis of compound of formula (Z) or a salt thereof, wherein, R, R1, R2, R3 and R10 are as defined in the detailed description. The process further comprises the synthesis of an anthranilic diamide compound of formula (I).

Improved synthesis process of 2-amino-5-chloro-N, 3-dimethylbenzamide

-

Paragraph 0031; 0035, (2021/03/11)

The invention discloses an improved synthesis process of 2-amino-5-chloro-N, 3-dimethylbenzamide, which comprises the following steps: preparing an instrument and a reagent for synthesizing 2-amino-5-chloro-N, 3-dimethylbenzamide, synthesizing 12-amino-3-methylbenzoic acid in a three-neck flask, adding ferric trichloride hexahydrate and activated carbon, stirring, heating, reacting, cooling, filtering, adding 2328-methyl-2H-3, 1-benzoxazine-2, 4(1H)-dione (MAD, 3) into a three-necked flask, adding 2-amino-3-methylbenzoic acid (MAA), pyridine and nitrile, heating under stirring until the reaction is completed, adding the reaction solution obtained in the second step into the three-neck flask, heating under stirring, then dropwise adding a mixed solution of sulfonyl chloride and acetonitrile, carrying out heat preservation reaction, then cooling to room temperature, directly filtering the reaction solution, and distilling the filtered filtrate to obtain 3-dimethylbenzamide. According tothe method for preparing the 2-amino-5-chloro-N, 3-dimethylbenzamide, the working procedure is simple and perfect in the process of preparing the 2-amino-5-chloro-N, 3-dimethylbenzamide, the preparation time can be well shortened, and the product quality is guaranteed.

Synthetic method of chlorantraniliprole pesticide intermediate 2 - amino -5 - chlorine - N and 3 -dimethylbenzamide

-

, (2021/10/05)

The invention relates to a synthetic method of a chlorantraniliprole pesticide intermediate 2 - amino -5 - chlorine - N and 3 -dimethylbenzamide. Chloro, formylation gave 2 - amino -5 - chloro - N, 3 - dimethyl. The method has the advantages of simple reaction, low cost and high yield, and is a method suitable for industrial production.

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