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317374-08-6 Usage

Chemical Properties

off-white to white powder

Check Digit Verification of cas no

The CAS Registry Mumber 317374-08-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,1,7,3,7 and 4 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 317374-08:
(8*3)+(7*1)+(6*7)+(5*3)+(4*7)+(3*4)+(2*0)+(1*8)=136
136 % 10 = 6
So 317374-08-6 is a valid CAS Registry Number.

317374-08-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methyl-4-[(2-methylbenzoyl)amino]benzoic acid

1.2 Other means of identification

Product number -
Other names 2-methyl-4-(2-methylbenzamide)benzoic acid

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:317374-08-6 SDS

317374-08-6Synthetic route

4-amino-2-methylbenzoic acid
2486-75-1

4-amino-2-methylbenzoic acid

ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
With pyridine In chloroform at 0 - 40℃; for 8h; Reagent/catalyst; Solvent; Temperature;95.6%
carbon monoxide
201230-82-2

carbon monoxide

2-bromo-5-(2-methylbenzoylamino)toluene
317374-07-5

2-bromo-5-(2-methylbenzoylamino)toluene

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: carbon monoxide; 2-bromo-5-(2-methylbenzoylamino)toluene With palladium diacetate; tributyl-amine; cesium acetate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 3h; carbonylation; Hydrolysis;
Stage #2: With sodium hydroxide In N,N-dimethyl-formamide; toluene at 20℃; for 0.5h;
81%
2-methyl-4-(2-methylbenzoylamino)acetophenone
928151-34-2

2-methyl-4-(2-methylbenzoylamino)acetophenone

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: 2-methyl-4-(2-methylbenzoylamino)acetophenone With sodium hypochlorite; water In isopropyl alcohol at 5 - 60℃; for 1h;
Stage #2: With hydrogenchloride In water at 20℃; Product distribution / selectivity;
77.2%
carbon monoxide
201230-82-2

carbon monoxide

7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one
160129-45-3

7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one

2-bromo-5-(2-methylbenzoylamino)toluene
317374-07-5

2-bromo-5-(2-methylbenzoylamino)toluene

A

MOP-21826
137973-76-3

MOP-21826

B

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
With cesium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide Heating;A n/a
B 75%
oxalyl dichloride
79-37-8

oxalyl dichloride

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: 2-methyl-N-m-tolylbenzamide; aluminum (III) chloride In dichloromethane at 3℃; for 0.166667h;
Stage #2: oxalyl dichloride In dichloromethane at 2 - 7℃; for 5h;
Stage #3: With hydrogenchloride; sodium hydroxide; water Product distribution / selectivity; more than 3 stages;
65.8%
1-{2-[2-methyl-4-(2-methylbenzoyl-amino)phenyl]-2-oxoethyl}pyridinium chloride

1-{2-[2-methyl-4-(2-methylbenzoyl-amino)phenyl]-2-oxoethyl}pyridinium chloride

1-{2-[4-methyl-2-(2-methylbenzoylamino)phenyl]-2-oxoethyl}pyridinium chloride
928151-38-6

1-{2-[4-methyl-2-(2-methylbenzoylamino)phenyl]-2-oxoethyl}pyridinium chloride

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: 1-{2-[2-methyl-4-(2-methylbenzoyl-amino)phenyl]-2-oxoethyl}pyridinium chloride; 1-{2-[4-methyl-2-(2-methylbenzoylamino)phenyl]-2-oxoethyl}pyridinium chloride With sodium hydroxide; water In methanol at 60 - 76℃; for 4h;
Stage #2: With hydrogenchloride In methanol; water at 60 - 76℃; pH=1; Product distribution / selectivity;
60.5%
2-chloro-2'-methyl-4'-(2-methylbenzoylamino)-acetophenone
928151-35-3

2-chloro-2'-methyl-4'-(2-methylbenzoylamino)-acetophenone

2-chloro-4'-methyl-2'-(2-methylbenzoylamino)aceto-phenone
928151-36-4

2-chloro-4'-methyl-2'-(2-methylbenzoylamino)aceto-phenone

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: 2-chloro-2'-methyl-4'-(2-methylbenzoylamino)-acetophenone; 2-chloro-4'-methyl-2'-(2-methylbenzoylamino)aceto-phenone With sodium hypochlorite; water In isopropyl alcohol at 10 - 20℃; for 0.5 - 1h;
Stage #2: With hydrogenchloride In water; isopropyl alcohol Product distribution / selectivity;
57%
tolvaptan
150683-30-0

tolvaptan

A

7-chloro-2,3-dihydro-1H-benzo[b]azepine
1316312-24-9

7-chloro-2,3-dihydro-1H-benzo[b]azepine

B

DM-4128

DM-4128

C

(4-amino-2-methylphenyl)(7-chloro-2,3-dihydro-1H-benzo[b]azepin-1-yl)methanone

(4-amino-2-methylphenyl)(7-chloro-2,3-dihydro-1H-benzo[b]azepin-1-yl)methanone

D

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; water In acetonitrile at 80℃; for 24h;
tolvaptan
150683-30-0

tolvaptan

A

DM-4128

DM-4128

B

N-(4-(7-chloro-2,3-dihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

N-(4-(7-chloro-2,3-dihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

C

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 80℃; for 17h;
methanol
67-56-1

methanol

tolvaptan
150683-30-0

tolvaptan

A

7-chloro-2,3-dihydro-1H-benzo[b]azepine
1316312-24-9

7-chloro-2,3-dihydro-1H-benzo[b]azepine

B

DM-4128

DM-4128

C

C11H14ClNO

C11H14ClNO

D

methyl 2-methyl-4-((2-methylbenzoyl)amino)benzoate

methyl 2-methyl-4-((2-methylbenzoyl)amino)benzoate

E

(4-amino-2-methylphenyl)(7-chloro-2,3-dihydro-1H-benzo[b]azepin-1-yl)methanone

(4-amino-2-methylphenyl)(7-chloro-2,3-dihydro-1H-benzo[b]azepin-1-yl)methanone

F

(4-amino-2-methylphenyl)(7-chloro-4-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)methanone

(4-amino-2-methylphenyl)(7-chloro-4-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)methanone

G

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 80℃; for 24h;
methanol
67-56-1

methanol

tolvaptan
150683-30-0

tolvaptan

A

DM-4128

DM-4128

B

C11H14ClNO

C11H14ClNO

C

N-(4-(7-chloro-2,3-dihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

N-(4-(7-chloro-2,3-dihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

D

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide at 80℃; for 17h;
2-methyl-4-aminobenzaldehyde
61594-81-8

2-methyl-4-aminobenzaldehyde

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride; sodium formate; formic acid / 3 h / 100 °C
2: water; sodium hydroxide / ethylene glycol / 6 h / 100 °C
3: pyridine / chloroform / 8 h / 0 - 40 °C
View Scheme
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trichlorophosphate / 6 h / 0 - 60 °C
2: hydroxylamine hydrochloride; sodium formate; formic acid / 3 h / 100 °C
3: water; sodium hydroxide / ethylene glycol / 6 h / 100 °C
4: pyridine / chloroform / 8 h / 0 - 40 °C
View Scheme
(4R,5R)-4,5-bis(methoxymethoxy)-7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepine
926035-26-9

(4R,5R)-4,5-bis(methoxymethoxy)-7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepine

2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

(4R,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
926035-30-5

(4R,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;81%
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

2-methyl-4-(2-methylbenzoylamino)benzoic acid chloride
331947-69-4

2-methyl-4-(2-methylbenzoylamino)benzoic acid chloride

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; thionyl chloride In dichloromethane for 0.5h; Heating;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 3h; Reflux;
With thionyl chloride In N,N-dimethyl acetamide at 0 - 25℃; for 2h; Reagent/catalyst; Temperature;
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

(4S,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
926035-31-6

(4S,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2; NMP / CH2Cl2 / 0.5 h / Heating
2: 85 percent / pyridine / CH2Cl2 / 20 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

(4S,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
926035-32-7

(4S,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2; NMP / CH2Cl2 / 0.5 h / Heating
2: 86 percent / pyridine / CH2Cl2 / 20 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

(4R,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
926035-33-8

(4R,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2; NMP / CH2Cl2 / 0.5 h / Heating
2: 83 percent / pyridine / CH2Cl2 / 20 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

DM-4111

DM-4111

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2; NMP / CH2Cl2 / 0.5 h / Heating
2: 85 percent / pyridine / CH2Cl2 / 20 °C
3: 82 percent / conc. HCl / methanol / 3.5 h / 60 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

(4S,5R)-7-chloro-4,5-dihydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

(4S,5R)-7-chloro-4,5-dihydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2; NMP / CH2Cl2 / 0.5 h / Heating
2: 86 percent / pyridine / CH2Cl2 / 20 °C
3: 87 percent / conc. HCl / methanol / 60 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

(4R,5S)-7-chloro-4,5-dihydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

(4R,5S)-7-chloro-4,5-dihydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2; NMP / CH2Cl2 / 0.5 h / Heating
2: 83 percent / pyridine / CH2Cl2 / 20 °C
3: 89 percent / conc. HCl / methanol / 60 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

N-(4-(7-chloro-5-hydroxy-2,2-dideutero-3,4,5-trihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide
1296212-19-5

N-(4-(7-chloro-5-hydroxy-2,2-dideutero-3,4,5-trihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 3 h / Reflux
2.1: triethylamine / dichloromethane / 4 h / 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
3.2: 0 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

N-(4-(5-(tert-butyldimethylsilyloxy)-7-chloro-2,2-dideutero-3,4,5-trihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide
1296212-26-4

N-(4-(5-(tert-butyldimethylsilyloxy)-7-chloro-2,2-dideutero-3,4,5-trihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 3 h / Reflux
2: triethylamine / dichloromethane / 4 h / 0 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

N-(4-(7-chloro-5-oxo-2,2-dideutero-3,4-dihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide
1296212-27-5

N-(4-(7-chloro-5-oxo-2,2-dideutero-3,4-dihydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 3 h / Reflux
2.1: triethylamine / dichloromethane / 4 h / 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
3.2: 0 °C
4.1: manganese(IV) oxide / dichloromethane / 8 h / Reflux
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

N-(4-(7-chloro-2,3-dihydro-5-hydroxy-2,2,4,4,5-pentadeutero-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide
1296212-20-8

N-(4-(7-chloro-2,3-dihydro-5-hydroxy-2,2,4,4,5-pentadeutero-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 3 h / Reflux
2.1: triethylamine / dichloromethane / 4 h / 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
3.2: 0 °C
4.1: manganese(IV) oxide / dichloromethane / 8 h / Reflux
5.1: d(4)-methanol; sodium hydroxide / 18 h / 20 °C / Inert atmosphere
6.1: d(4)-methanol; sodium borodeuteride / 2 h / 0 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

N-(4-(7-chloro-2,3-dihydro-5-oxo-2,2,4,4-tetradeutero-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide
1296212-28-6

N-(4-(7-chloro-2,3-dihydro-5-oxo-2,2,4,4-tetradeutero-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 3 h / Reflux
2.1: triethylamine / dichloromethane / 4 h / 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
3.2: 0 °C
4.1: manganese(IV) oxide / dichloromethane / 8 h / Reflux
5.1: d(4)-methanol; sodium hydroxide / 18 h / 20 °C / Inert atmosphere
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / N,N-dimethyl acetamide / 2 h / 0 - 25 °C
2: 2,6-dimethylpyridine / N,N-dimethyl acetamide; water / 2 h / 0 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

C34H32ClN3O4

C34H32ClN3O4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / toluene / 3 h / Reflux
1.2: 1 h
2.1: thionyl chloride / dichloromethane / 4 h / Reflux
3.1: pyridine / ethyl acetate / 20 °C
4.1: potassium borohydride; ethanol / 1 h / 25 - 35 °C
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

C24H21ClN2O3

C24H21ClN2O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: thionyl chloride / toluene / 3 h / Reflux
1.2: 1 h
2.1: thionyl chloride / dichloromethane / 4 h / Reflux
View Scheme
2-methyl-4-(2-methylbenzoylamino)benzoic acid
317374-08-6

2-methyl-4-(2-methylbenzoylamino)benzoic acid

C34H30ClN3O4

C34H30ClN3O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / toluene / 3 h / Reflux
1.2: 1 h
2.1: thionyl chloride / dichloromethane / 4 h / Reflux
3.1: pyridine / ethyl acetate / 20 °C
View Scheme

317374-08-6Relevant articles and documents

Beneficial effect of cesium salts on Pd-catalyzed hydroxycarbonylation

Torisawa, Yasuhiro,Nishi, Takao,Minamikawa, Jun-ichi

, p. 2493 - 2495 (2000)

A Pd(0)-catalyzed hydroxycarbonylation of the aryl bromide was effectively carried out in the presence of some Cs salts such as cesium carbonate, cesium bicarbonate, and cesium acetate in wet DMF solution. For the understanding of their function, an oxy-coordinated intermediate arising from a Cs-oxygen-Pd interaction has been postulated, which is likely to be responsible for related Cs assisted catalytic processes. (C) 2000 Elsevier Science Ltd.

Characterization of the stress degradation products of tolvaptan by UPLC-Q-TOF-MS/MS

Patel, Prinesh N.,Rajesh Kumar,Gananadhamu,Srinivas

, p. 21142 - 21152 (2015/03/30)

Tolvaptan (TVT) is a selective, competitive vasopressin receptor 2 antagonist used to treat hyponatremia. TVT was subjected to forced degradation under hydrolysis, oxidation, dry heat and photolysis conditions, in accordance with the ICH guideline Q1A (R2). The degradation products (DPs) formed have been characterized through UPLC-PDA and UPLC-Q-TOF-MS/MS studies. The chromatographic separation was achieved on an Acquity UPLC HSS T3 column (100 × 2.1 mm, 1.7 μm) with a mobile phase containing a gradient mixture of solvents A (0.1% formic acid) and B (acetonitrile) at a flow rate of 0.3 ml min-1 at 30 °C. The detection wavelength was set at 266 nm. The drug degraded under acid hydrolysis, base hydrolysis and oxidative conditions to form a total of 7 DPs. When methanol was used as the co-solvent during stress degradation, four additional DPs were formed which were absent when acetonitrile was used as the co-solvent. Comparison of the fragmentation pattern of the DPs with that of the drug helped in the elucidation of the structures of all the degradation products. The degradation pathway of the drug was established, which was duly justified by the mechanistic explanation. The developed UPLC method was validated as per ICH guidelines.

Aminocarbonylation route to tolvaptan

Torisawa, Yasuhiro,Furuta, Takuya,Nishi, Takao,Aki, Shinji,Minamikawa, Jun-ichi

, p. 6455 - 6458 (2008/03/14)

Pd-catalyzed aminocarbonylation between aryl bromide and NH-benzazepinone was effectively carried out to furnish the key intermediate for tolvaptan (up to 85%) in one step.

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