4389-45-1

Basic information

• Product Name: 3-Methylanthranilic acid
• Synonyms: Benzoic acid, 2-amino-3-methyl-;m-Toluic acid, 2-amino-;2-AMINO-3-METHYLBENZOIC ACID;2-AMINO-M-TOLUIC ACID;3-METHYL-2-AMINOBENZOIC ACID;3-METHYLANTHRANILIC ACID;METHYLANTHRANILIC ACID;2-Amino-3-Methybenzoic Acid
• CAS NO: 4389-45-1
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 224-505-2
• Product Categories: CARBOXYLICACID;FINE Chemical & INTERMEDIATES;Amines;blocks;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid;Organic acids;Carboxylic Acids;Phenyls & Phenyl-Het
• Mol File: 4389-45-1.mol
• Article Data: 34

Chemical Properties

• Melting Point: 174-177 °C(lit.)
• Boiling Point: 273.17°C (rough estimate)
• Flash Point: 144.4 °C
• Appearance: Pink to gray-brown/Crystalline Powder
• Density: 1.2023 (rough estimate)
• Vapor Pressure: 0.000188mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol
• PKA: 5.01±0.10(Predicted)
• BRN: 2359694
• CAS DataBase Reference: 3-Methylanthranilic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylanthranilic acid(4389-45-1)
• EPA Substance Registry System: 3-Methylanthranilic acid(4389-45-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 4389-45-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4389-45-1 differently. You can refer to the following data:
1. 2-Amino-3-methylbenzoic acid is a metabolite of Lidocaine, an antiarrythmic drug that is used to treat patients with ventricular fibrillation. 2-Amino-3-methylbenzoic acid has potential herbicidal activity, and is also used as a reagent to synthesize Ropicavaine, a local anasthetic.
2. 2-Amino-3-methylbenzoic acid is a metabolite of Lidocaine (L397800), an antiarrythmic drug that is used to treat patients with ventricular fibrillation. 2-Amino-3-methylbenzoic acid has potential herbicidal activity, and is also used as a reagent to synthesize Ropicavaine (R675000), a local anasthetic.

Chemical Properties

pink to grey-brown crystalline powder

InChI:InChI=1/C8H9NO2/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4H,9H2,1H3,(H,10,11)

Synthetic route

3-methyl-2-nitrobenzoic acid (5437-38-7) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr;	99%
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 25857.4 Torr;	99%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr;	99%

2-chloro-3-methylbenzoic acid (15068-35-6) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With ammonia; sodium carbonate; copper(l) chloride In dimethyl sulfoxide at 130 - 150℃; for 5h;	93.1%

7-methyl-1H-indole-2,3-dione (1127-59-9) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide	90%
With potassium chloride; dihydrogen peroxide; sodium hydroxide In water at 0 - 20℃; for 2.25h;	80%
	60%

3-methyl-2-nitrobenzoyl chloride (50424-93-6) + methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate (83325-79-5) → 3-methylantranilic acid (4389-45-1) + methyl 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilate (83334-85-4)

Conditions	Yield
With lithium hydroxide In water; benzene	A n/a B 61%

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione (857203-66-8) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With potassium hydroxide

methanol (67-56-1) + 7-methyl-1H-indole-2,3-dione (1127-59-9) → methyl 2-amino-3-methylbenzoate (22223-49-0) + 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With dihydrogen peroxide; sodium methylate 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;

7-methyl-1H-indole-2,3-dione (1127-59-9) + butan-1-ol (71-36-3) → 3-methylantranilic acid (4389-45-1) + 3-Methylanthranilsaeure-n-butylester (79101-84-1)

Conditions	Yield
With dihydrogen peroxide; sodium hydride 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;

3-methyl-2-nitrobenzonitrile (1885-77-4) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
(i) H2, Pd-C, (ii) aq. NaOH; Multistep reaction;

3-methyl-2-nitrobenzoyl chloride (50424-93-6) + 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid (78877-00-6) → 3-methylantranilic acid (4389-45-1) + 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilic acid (83325-80-8)

Conditions	Yield
With lithium hydroxide In water; benzene Title compound not separated from byproducts;

7-methyl-1H-indole-2,3-dione (1127-59-9) + dihydrogen peroxide (7722-84-1) + alkali → 3-methylantranilic acid (4389-45-1)

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione (857203-66-8) + aqueous NaOH → 3-methylantranilic acid (4389-45-1) + o-toluidine (95-53-4)

3-methyl-2-nitrobenzoic acid (5437-38-7) + ammonia (7664-41-7) + iron(II) sulfate → 3-methylantranilic acid (4389-45-1)

hydrogenchloride (7647-01-0) + 3-methyl-2-nitrobenzoic acid (5437-38-7) + tin → 3-methylantranilic acid (4389-45-1)

ethanol (64-17-5) + 3-methyl-2-nitrobenzoic acid (5437-38-7) + zinc dust + alkali → 3-methylantranilic acid (4389-45-1)

hydrogenchloride (7647-01-0) + 3-methyl-2-nitrobenzoic acid (5437-38-7) + tin → 3-methylantranilic acid (4389-45-1) + o-toluidine (95-53-4)

3-methyl-2-nitrobenzonitrile (1885-77-4) + alcoholic ammonium sulfide → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
at 100℃; im Rohr;

(2-amino-3-methyl-phenyl)-glyoxylic acid (859770-30-2) + dihydrogen peroxide (7722-84-1) + diluted NaOH-solution → 3-methylantranilic acid (4389-45-1)

(2-amino-3-methyl-phenyl)-glyoxylic acid (859770-30-2) + sodium perborate + diluted NaOH-solution → 3-methylantranilic acid (4389-45-1)

m-Toluic acid (99-04-7) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 46 percent / HNO3 / 1 h / -10 °C 2: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: fuming nitric acid 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: fuming nitric acid 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: nitric acid / -10 - -5 °C 2: palladium 10% on activated carbon; hydrogen / methanol View Scheme
Multi-step reaction with 2 steps 1: nitric acid / 1 h / -10 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 50 °C View Scheme

m-Toluic acid (99-04-7) + aqueous ammonium polysulfide → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / fuming nitric acid / 1 h / -10 °C 2: 89 percent / tin, hydrochloric acid / ethanol / 1.5 h / 70 °C View Scheme

2-(hydroxyimino)-N-(2-methylphenyl)acetamide (1132-03-2) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86percent H2SO4 / 1) 55 deg C, 10 min, 2) 75 deg C, 30 min 2: H2O2, NaOH View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 0.33 h / 80 °C 2: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C View Scheme
Multi-step reaction with 2 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 View Scheme

3-Methylbenzonitrile (620-22-4) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated hydrochloric acid / im Druckrohr 2: fuming nitric acid 3: tin; hydrochloric acid View Scheme

3-Methyl-2-nitrobenzenecarboxamide (60310-07-8) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3 2: (i) H2, Pd-C, (ii) aq. NaOH View Scheme

o-toluidine (95-53-4) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 55 °C 2: sulfuric acid / neat (no solvent) / 55 - 80 °C 3: sodium hydroxide; dihydrogen peroxide; potassium chloride / water / 2.25 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 0.17 h / Reflux 2: sulfuric acid / 0.83 h / 70 - 80 °C 3: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C View Scheme
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium sulfate; hydrogenchloride / water / 12 h / 55 °C / Inert atmosphere 2: sulfuric acid / 0.67 h / Heating; Inert atmosphere 3: dihydrogen peroxide; sodium hydroxide / water / 5.5 h / 80 °C / Inert atmosphere View Scheme

3-methyl-DL-kynurenine (1446522-57-1) → L-alanin (56-41-7) + 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With Pseudomonas fluorescens kynureninase In aq. phosphate buffer at 37℃; pH=8; Kinetics; Enzymatic reaction;

ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate (582319-05-9) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / water / 2 h / 55 - 60 °C 2: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice 3: hydrogenchloride / water / 4 h / Reflux 4: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme

ethyl 7-methylindole-3-(3-acetamido-3-carboethoxy)butanoate → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice 2: hydrogenchloride / water / 4 h / Reflux 3: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme

ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(2-formamido-3-methylphenyl)pentanoate (1446522-63-9) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 4 h / Reflux 2: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme

methyl 2-amino-3-methylbenzoate (22223-49-0) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; ethanol; water at 50℃; for 3h; Inert atmosphere;

3-methylantranilic acid (4389-45-1) → 2-amino-3-methylbenzyl alcohol (57772-50-6)

Conditions	Yield
Stage #1: 3-methylantranilic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: With water; sodium hydroxide In tetrahydrofuran	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h;	97%

3-methylantranilic acid (4389-45-1) → 2-amino-5-bromo-3-methylbenzoic acid (206548-13-2)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1h;	100%
With bromine; acetic acid at 20 - 25℃;	97%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h;	95.6%

3-methylantranilic acid (4389-45-1) + methyl iodide (74-88-4) → methyl 2-amino-3-methylbenzoate (22223-49-0)

Conditions	Yield
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;	100%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 18.5h;	92%
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 24h;	77%
Stage #1: 3-methylantranilic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 24h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;

3-carboxyphthalic anhydride (3786-39-8) + 3-methylantranilic acid (4389-45-1) → C17H11NO6 (1158834-44-6, 1159266-95-1, 1159266-96-2)

Conditions	Yield
at 150℃; for 12h;	100%

6-[(R)-5-(3-amino-propyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one (1221280-89-2) + 3-methylantranilic acid (4389-45-1) → 2-amino-4-methyl-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-yl]-propyl}-benzamide

Conditions	Yield
	100%

3-methylantranilic acid (4389-45-1) → 2-amino-5-chloro-3-methylbenzoic acid (20776-67-4)

Conditions	Yield
With chlorine In 1,2-dichloro-ethane at 50℃; for 3h; Solvent;	98.1%
With N-chloro-succinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h;	97.8%
With N-chloro-succinimide In N,N-dimethyl-formamide at 75℃;	91%

3-methylantranilic acid (4389-45-1) + ortho-chlorobenzoic acid (118-91-2) → 2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid (80841-45-8)

Conditions	Yield
With copper; potassium carbonate; copper(I) bromide In various solvent(s) at 160℃; for 0.5h;	98%

piperidine (110-89-4) + 3-methylantranilic acid (4389-45-1) → (2-amino-3-methylphenyl)(piperidin-1-yl)methanone

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 16h;	98%

3-methylantranilic acid (4389-45-1) + 4-Chlorophenylsulfonyl isocyanate (5769-15-3) → 3-(4-chlorobenzenesulfonyl)-8-methyl-2,4(1H,3H)-quinazolinedione

Conditions	Yield
	98%

3-methylantranilic acid (4389-45-1) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → C17H15NO4 (698393-13-4)

Conditions	Yield
at 110℃; for 16h; Inert atmosphere; neat (no solvent);	98%

3-methylantranilic acid (4389-45-1) → 2-amino-3-methylbenzamide (1885-32-1)

Conditions	Yield
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide	98%
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere;	98%
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere;	98%

p-chlorophenyl isoselenocyanate (14223-48-4) + 3-methylantranilic acid (4389-45-1) → 2-(4-chlorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 4.5h;	98%

3-methylantranilic acid (4389-45-1) → 2-amino-5-iodo-3-methylbenzoic acid (108857-24-5)

Conditions	Yield
With dipotassium peroxodisulfate; iodine In tetrachloromethane at 77℃; for 6h;	97.7%
With N-iodo-succinimide In N,N-dimethyl-formamide at 20 - 80℃; for 2h;	97%
With N-iodo-succinimide In N,N-dimethyl-formamide at 75℃; for 1h; Inert atmosphere;	96%

3-methylantranilic acid (4389-45-1) → 6,6'-dimethyl-1,1'-biphenyl-2,2'-dicarboxylic acid (57024-47-2, 108146-85-6, 19634-85-6)

Conditions	Yield
Stage #1: 3-methylantranilic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With copper(I) In water	97%
With Cu(I)-salt; sodium nitrite	78%
Stage #1: 3-methylantranilic acid With sodium hydroxide; sodium nitrite at 0℃; for 0.5h; Stage #2: With hydroxyammonium sulfate; copper(II) sulfate In water	72%

3-methylantranilic acid (4389-45-1) + [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate (189999-35-7) → 2′-iodo-[1,1′-biphenyl]-2-yl benzoate

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; sodium carbonate In 1,4-dioxane at 95℃; for 17h; Molecular sieve; Green chemistry;	97%

phosgene (75-44-5) + 3-methylantranilic acid (4389-45-1) → 6-methylisatoic anhydride (66176-17-8)

Conditions	Yield
In 1,4-dioxane; benzene Ambient temperature;	96%
With sodium hydrogencarbonate In toluene at 0 - 20℃; for 0.25h;	86%

3-methylantranilic acid (4389-45-1) + α,α-diphenylsuccinic acid anhydride (14702-32-0) → 2-(2,5-dioxo-3,3-diphenylpyrrolidin-1-yl)-3-methylbenzoic acid (297757-12-1, 297757-33-6, 297757-34-7)

Conditions	Yield
at 150℃; for 12h; Condensation;	96%
at 150℃; neat (no solvent, solid phase);

3-methylantranilic acid (4389-45-1) + formamidine acetic acid (3473-63-0) → 8-methyl-4-quinazolinone

Conditions	Yield
In formamide at 160℃; for 12h;	96%
With formamide at 160℃;	96%

3-methylantranilic acid (4389-45-1) + 1-fluoro-4-isoselenocyanatobenzene (154592-60-6) → 2-(4-fluorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 4.5h;	96%

3-methylantranilic acid (4389-45-1) + cyclohexanecarbaldehyde (2043-61-0) → 2-cyclohexyl-8-methyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions	Yield
With acetic acid In ethanol for 6h; Reflux;	96%

bis(trichloromethyl) carbonate (32315-10-9) + 3-methylantranilic acid (4389-45-1) → 6-methylisatoic anhydride (66176-17-8)

Conditions	Yield
In 1,4-dioxane for 6.5h; Reflux;	95%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane	94%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane	94%

3-methylantranilic acid (4389-45-1) + 1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) → C16H17NO4 (1185155-84-3)

Conditions	Yield
at 110℃; for 10h; Inert atmosphere; neat (no solvent);	95%

3-methylantranilic acid (4389-45-1) + 4-bromophenyl isoselenocyanate (147695-56-5) → 2-(4-bromophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 4.5h;	95%

3-methylantranilic acid (4389-45-1) → 2-amino-5-bromo-3-methylbenzoic acid hydrobromide

Conditions	Yield
With bromine; acetic acid In dichloromethane at 20℃; for 1h;	95%

3-methylantranilic acid (4389-45-1) + acetic anhydride (108-24-7) → 2-acetylamino-3-methylbenzoic acid (67081-69-0)

Conditions	Yield
for 2h; Reflux;	94%
for 2h; Heating;	87%
for 1h; Acetylation; Heating;	85%
at 60℃; Reflux;

3-methylantranilic acid (4389-45-1) → 6-methylisatoic anhydride (66176-17-8)

Conditions	Yield
With bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 16.5h;	94%
Multi-step reaction with 2 steps 1: triethylamine; dmap / acetonitrile / 2 h / 20 °C 2: 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 0.17 h / 20 °C View Scheme

3-methylantranilic acid (4389-45-1) + formamidine acetic acid (3473-63-0) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 8-methylquinazolin-4(3H)-one (19181-54-5)

Conditions	Yield
at 180℃; for 3h;	94%

4-pentynoic acid (6089-09-4) + 3-methylantranilic acid (4389-45-1) → 3a,9-dimethyl-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione (1227624-59-0)

Conditions	Yield
With Echavarren's catalyst In 1,1-dichloroethane at 120℃; for 12h; Sealed vial;	93%

Upstream product

• 1127-59-9 7-methyl-1H-indole-2,3-dione 
• 1885-77-4 3-methyl-2-nitrobenzonitrile 
• 50424-93-6 3-methyl-2-nitrobenzoyl chloride 
• 78877-00-6 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid 
• 83325-79-5 methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate 
• 857203-66-8 8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 7664-41-7 ammonia 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 859770-30-2 (2-amino-3-methyl-phenyl)-glyoxylic acid 
• 7722-84-1 dihydrogen peroxide 
• 99-04-7 m-Toluic acid 
• 95-53-4 o-toluidine 

Downstream Products

• 108716-22-9 3-methyl-2-o-toluidino-benzoic acid 
• 66176-17-8 6-methylisatoic anhydride 
• 73262-66-5 2-Amino-3-methyl-benzoic acid propyl ester 
• 142141-38-6 2-amino-3-methyl-N-propylbenzamide 
• 80841-45-8 2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 78876-98-9 3-methyl-N-(3-methyl-2-nitrobenzoyl)anthranilic acid 
• 77149-11-2 3-methyl-2-mercaptobenzoic acid 
• 78876-99-0 methyl 3-methyl-N-methyl-N-(3-methyl-2-nitrobenzoyl)anthranilate 
• 64465-16-3 7,12-Dibutyl-8-methyl-benzo[k]fluoranthene 
• 65911-44-6 2-diazonio-3-methylbenzoate 
• 206531-05-7 2-<<5-chloro-2-(methoxycarbonyl)phenyl>amino>-3-methylbenzoic acid 
• 95-53-4 o-toluidine 
• 297757-12-1 2-(2,5-dioxo-3,3-diphenylpyrrolidin-1-yl)-3-methylbenzoic acid 

Relevant articles and documents

Preparation method of 2-amino-3-methyl-5-chlorobenzoic acid

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention comprises the steps of mixing m-toluic acid and nitric acid, and carrying out nitration reaction to obtain 2-nitro-3-methyl benzoic acid, wherein the mass concentration of the nitric acid is 60-75%; mixing the 2-nitro-3-methyl benzoic acid, a hydrogenation reduction reaction solvent and a hydrogenation catalyst, and carrying out hydrogenation reduction reaction in a hydrogen atmosphere to obtain 2-amino-3-methyl benzoic acid; and mixing the 2-amino-3-methyl benzoic acid, a chlorination reagent, benzoyl peroxide and a chlorination reaction solvent, and carrying out a chlorination reaction to obtain the 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention has the advantages of cheap and easily available reaction raw materials, high product yield and high purity, and is easy for industrial production.

AN IMPROVED HYDROGENATION PROCESS USING A TRANSITION METAL COMPLEX CATALYST

The present invention relates to the process of reduction of compound of formula (II) by using a transition metal complex (Z) as a catalyst for hydrogenation reactions to get compound of formula (I). More particularly, the present invention relates to an improved process for the preparation of a compound (I) (as described herein) or a salt thereof; comprising hydrogenation of the compound (II) (as described herein) using a transition metal complex catalyst (Z).

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

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.