89-77-0

Basic information

• Product Name: 2-Amino-4-chlorobenzoic acid
• Synonyms: 4-CHLORO-2-AMINOBENZOIC ACID;3-AMINO-4-CARBOXY-1-CHLOROBENZENE;2-AMINO-4-CHLOROBENZOIC ACID;2-CARBOXY-5-CHLOROANILINE;2,4-ACBA;4-chloroanthranil acid;p-Chloro-o-Amino Benzoic Acid;4-ChloroanthranilicAcid98%
• CAS NO: 89-77-0
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58
• EINECS: 201-938-5
• Product Categories: FINE Chemical & INTERMEDIATES;Amines;blocks;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid series;API Intermediate
• Mol File: 89-77-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 231-233 °C(lit.)
• Boiling Point: 250°C (rough estimate)
• Flash Point: 166.2 °C
• Appearance: Beige to light brown/Powder
• Density: 1.3246 (rough estimate)
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: almost transparency in 1mol/L NaOH
• PKA: 4.71±0.10(Predicted)
• Water Solubility: slightly soluble
• BRN: 743349
• CAS DataBase Reference: 2-Amino-4-chlorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-chlorobenzoic acid(89-77-0)
• EPA Substance Registry System: 2-Amino-4-chlorobenzoic acid(89-77-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: DG1570000
• Hazardous Substances Data: 89-77-0(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Uses

2-Amino-4-chlorobenzoic Acid is used in the preparation of quinazolinone derivatives observed to be useful in the treatment of Alzheimer’s disease. Also it aids in the synthesis of non-nucleoside, thumb pocket 2 HCV NS5B polymerase inhibitors used in Hepatitis C therapy.

InChI:InChI=1/C7H6ClNO2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3H,9H2,(H,10,11)/p-1

Synthetic route

2,4 dichlorobenzoic acid (50-84-0) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With ammonium hydroxide at 126 - 129℃; under 3800 - 9120 Torr; for 6h;	88%
With ammonia; copper at 120℃;

2,4-dichlorobenzoic acid potassium salt (66909-52-2) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With ammonium hydroxide; copper diacetate at 126 - 129℃; for 10h;	68%

4-chloro-2-nitro-benzoic acid (6280-88-2) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With tin(II) chloride dihdyrate In ethanol for 1h; Inert atmosphere;	23%
With platinum Hydrogenation;
With ammonia; iron(II) sulfate

6-chloroisatin (6341-92-0) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

2-amino-4-chlorobenzamide (5900-59-4) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With sulfuric acid

7-chloro-3-(3-chlorophenyl)quinazoline-2,4(1H,3H)-dione (61680-22-6) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With potassium hydroxide

4-chlorophthalamide (96385-49-8) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With alkaline aqueous potassium hypobromite

2-acetylamino-4-chlorobenzoic acid (5900-56-1) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With hydrogenchloride Zers. des entstandenen Hydrochlorids mit Natriumacetat;

methanol (67-56-1) + 6-chloroisatin (6341-92-0) → 2-amino-4-chloro-benzoic acid methyl ester (5900-58-3) + 2-Amino-4-chlorobenzoic acid (89-77-0)

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

4-chlorophthalimide (7147-90-2) + alkaline hypochlorite → 2-Amino-4-chlorobenzoic acid (89-77-0) + N-<5-chloro-2-amino-benzoyl>-<5-chloro-2-amino-benzoic acid >(?)

4-chloro-phthalic acid imide → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With potassium hydroxide; sodium hypochlorite

2,4 dichlorobenzoic acid (50-84-0) + ammonia (7664-41-7) + copper → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
at 120℃;

methyl 2,4-dichlorobenzoate (35112-28-8) + ammonium hydroxide → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
at 120℃;

4-chlorophthalamide (96385-49-8) + alkaline aqueous potassium hypobromite → 2-Amino-4-chlorobenzoic acid (89-77-0)

4-chloro-phthalic acid imide → 2-(2-Amino-5-chlor-benzoylamino)-5-chlor-benzoesaeure (91164-43-1) + 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With potassium hydroxide; sodium hypochlorite

m-chlorophenyl isocyanate (2909-38-8) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; NaCl 2: aqueous KOH View Scheme

4-chloro-2-nitrobenzonitrile (34662-32-3) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: iron (II)-sulfate; ammonia View Scheme
Multi-step reaction with 2 steps 1: iron; diluted acetic acid / <70 2: sulfuric acid View Scheme

4-Chloro-2-nitroaniline (89-63-4) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 2: sulfuric acid 3: iron (II)-sulfate; ammonia View Scheme
Multi-step reaction with 3 steps 2: iron; diluted acetic acid / <70 3: sulfuric acid View Scheme

N-(5-chloro-2-methylphenyl)acetamide (5900-55-0) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate; magnesium sulfate 2: concentrated hydrochloric acid / Zers. des entstandenen Hydrochlorids mit Natriumacetat View Scheme

para-chlorobenzoic acid (74-11-3) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / water / 6 h / 60 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / ethanol / 6 h / Reflux View Scheme

2-amino-4-chloro-benzoic acid methyl ester (5900-58-3) → 2-Amino-4-chlorobenzoic acid (89-77-0)

Conditions	Yield
With water; sodium hydroxide In ethanol for 1.5h; Reflux;

urea (57-13-6) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloroquinazoline-2,4-dione (13165-35-0)

Conditions	Yield
at 200℃; for 1h;	100%
at 200℃; for 2h;	85%
With sodium hydroxide In water for 120h; Heating;	33%

(2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (127000-91-3) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-benzamide (206350-07-4)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 18h; Ambient temperature;	100%
With 2,6-dimethylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	32 mg
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;

2-Amino-4-chlorobenzoic acid (89-77-0) → (2-amino-4-chlorophenyl)methanol (37585-16-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%
Stage #1: 2-Amino-4-chlorobenzoic 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%

4-piperidone hydrochloride (41979-39-9) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 1-(2-amino-4-chlorobenzoyl)piperidin-4-one (1451261-87-2)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	100%

2-Amino-4-chlorobenzoic acid (89-77-0) + trimethyl orthoformate (149-73-5) → 7-chloroquinazolin-4(1H)-one (31374-18-2)

Conditions	Yield
With ammonia In methanol at 120℃; for 2h;	99%
With ammonium acetate In methanol at 120℃; for 3h;	92%

pyrrolidine (123-75-1) + 2-Amino-4-chlorobenzoic acid (89-77-0) → (2-amino-4-chloro-phenyl)-pyrrolidin-1-yl-methanone

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	99%

2-Bromoacetyl bromide (598-21-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 2-(2-bromoacetamido)-4-chlorobenzoic acid (178270-85-4)

Conditions	Yield
In 1,4-dioxane; N,N-dimethyl-formamide at 0 - 20℃;	99%
In 1,4-dioxane; N,N-dimethyl-formamide at 0 - 20℃;	99%
In 1,4-dioxane; N,N-dimethyl-formamide at 0 - 20℃;	99%
In 1,4-dioxane; N,N-dimethyl-formamide at 20℃;

cyclohexanone (108-94-1) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 6,9-dichloro-1,2,3,4-tetrahydroacridine (5396-25-8)

Conditions	Yield
With trichlorophosphate for 3h; Heating / reflux;	98.2%
With trichlorophosphate for 2h; Cyclization; condensation; Heating;	93%
With trichlorophosphate for 2h; Heating;	93%

2-Amino-4-chlorobenzoic acid (89-77-0) → 2-mercapto-4-chlorobenzoic acid (20324-49-6)

Conditions	Yield
Stage #1: 2-Amino-4-chlorobenzoic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With potassium ethyl xanthogenate In water at 75 - 80℃; for 0.5h; Stage #3: With hydrogenchloride; sodium hydroxide; water; sodium hydrogensulfite more than 3 stages;	98%
Stage #1: 2-Amino-4-chlorobenzoic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0℃; for 1h; Stage #2: With potassium ethyl xanthogenate; sodium hydroxide In water at 65℃;	63%
With hydrogenchloride; sodium disulfide; acetic acid; zinc; sodium nitrite Multistep reaction;

2-Amino-4-chlorobenzoic acid (89-77-0) → 2-amino-5-bromo-4-chlorobenzene carboxylic acid (50419-88-0)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 1h;	98%
With bromine In methanol at -15 - -10℃; for 2h; Concentration;	92%
With bromine In methanol at -78℃; for 2h;	62%

acetic anhydride (108-24-7) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloro-2-methyl-4H-3,1-benzoxazin-4-one (708-73-6)

Conditions	Yield
at 150℃; for 0.333333h; Microwave irradiation; Sealed tube;	97%
for 2h; Acetylation; cyclization; condensation; Heating;	81%
Reflux;	81%

diazomethane (186581-53-3, 908094-01-9) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 2-amino-4-chloro-benzoic acid methyl ester (5900-58-3)

Conditions	Yield
In diethyl ether at 20℃; for 1h;	97%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloro-3,4-dihydroquinazolin-4-one (31374-18-2)

Conditions	Yield
With acetic acid; diethylamine at 150℃; for 2h; Product distribution / selectivity;	96.1%
With montmorillonite K-10 for 0.0666667h; microwave irradiation;	94%
at 130 - 160℃; for 5h;	90.7%

4-Chlorophenyl isothiocyanate (2131-55-7) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloro-3-(4-chlorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (118449-37-9)

Conditions	Yield
In ethanol Heating;	95%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloro-4-hydroxyquinazoline (31374-18-2)

Conditions	Yield
at 160℃; for 4h;	95%
1.) 120 deg C, 2 h; 2.) 170 deg C, 2 h;
at 200℃; for 6h;

(Chlorocarbonyl-phenyl-methyl)-carbamic acid benzyl ester (61464-95-7) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 2-(2-benzyloxycarbonylamino-2-phenyl-acetylamino)-4-chloro-benzoic acid (350238-17-4)

Conditions	Yield
In tetrahydrofuran	95%

2-Amino-4-chlorobenzoic acid (89-77-0) → ammonium 4-chloroanthranilate

Conditions	Yield
With ammonia In methanol at 20℃; for 2h;	95%

benzyl-methyl-amine (103-67-3) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 2-amino-N-benzyl-4-chloro-N-methyl-benzamide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃;	95%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 4-chlorpyridine hydrochloride (7379-35-3) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 1-(2-carboxy-4-chlorophenyl)pyrrole (55540-33-5)

Conditions	Yield
In 1,4-dioxane; water	95%

acetic acid (64-19-7) + 2-Amino-4-chlorobenzoic acid (89-77-0) + 2-(2-Aminoethoxy)ethanol (929-06-6) → C13H15ClN2O3 (1268696-00-9)

Conditions	Yield
With montmorillonite K 10 for 0.0333333h; Microwave irradiation;	95%

propionic acid (802294-64-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) + 2-(2-Aminoethoxy)ethanol (929-06-6) → C14H17ClN2O3 (1268695-99-3)

Conditions	Yield
With montmorillonite K 10 for 0.0333333h; Microwave irradiation;	95%

formamidine acetic acid (3473-63-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloro-3,4-dihydroquinazolin-4-one (31374-18-2)

Conditions	Yield
In water Microwave irradiation;	95%
In 2-methoxy-ethanol at 120℃; for 16h;	88.1%
In 2-methoxy-ethanol Reflux;
In 2-methoxy-ethanol for 18h; Reflux;
In 2-methoxy-ethanol at 130℃;

bis(trichloromethyl) carbonate (32315-10-9) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 4-chloroisatoic anhydride (40928-13-0)

Conditions	Yield
In tetrahydrofuran at 20℃; Inert atmosphere;	94.4%
In tetrahydrofuran at 20℃; for 18h;	83%
With pyridine In dichloromethane; acetonitrile at 50℃; for 2h;	74%

2-Amino-4-chlorobenzoic acid (89-77-0) + trifluoroacetic anhydride (407-25-0) → 7-chloro-2-(trifluoromethyl)-4H-benzo[d][1,3]-oxazin-4-one (42772-89-4)

Conditions	Yield
at 20℃; for 3h;	94.4%

methanol (67-56-1) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 2-amino-4-chloro-benzoic acid methyl ester (5900-58-3)

Conditions	Yield
With sulfuric acid for 12h; Heating;	94%
With thionyl chloride at -5℃; for 4.5h; Temperature; Reflux; Industrial scale;	83%
With thionyl chloride at 0 - 5℃; for 24h; Reflux;	82%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 2-Amino-4-chlorobenzoic acid (89-77-0) → methyl 4-chloro-2-(N,N-dimethyl-N'-formamidinyl)benzoate (113290-36-1)

Conditions	Yield
In N,N-dimethyl-formamide Heating;	94%

formamidine acetic acid (3473-63-0) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloroquinazolin-4(1H)-one (31374-18-2)

Conditions	Yield
In ethyl methyl ether Reflux;	94%

phosgene (75-44-5) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 4-chloroisatoic anhydride (40928-13-0)

Conditions	Yield
With sodium carbonate In toluene at 20℃; Cycloaddition;	93%
In 1,4-dioxane at 40℃; for 1.5h;
In 1,4-dioxane at 20℃; for 1h;
In tetrahydrofuran; toluene at 20℃; for 24h; Inert atmosphere;

benzoyl chloride (98-88-4) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 7-chloro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one (7033-52-5)

Conditions	Yield
With pyridine for 0.5h; Acylation; cyclization; condensation;	93%
With pyridine at 0 - 20℃; for 3h;	70%
With pyridine at 20℃; for 12.5h; Time; Cooling with ice;	60.2%

phosgene (75-44-5) + sodium carbonate (497-19-8) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 4-chloroisatoic anhydride (40928-13-0) + 2-amino-4-chloro-5-nitrobenzamide (252232-80-7)

Conditions	Yield
In water; toluene	A 93% B n/a

Upstream product

• 5900-56-1 2-acetylamino-4-chlorobenzoic acid 
• 66909-52-2 2,4-dichlorobenzoic acid potassium salt 
• 7147-90-2 4-chlorophthalimide 
• 50-84-0 2,4 dichlorobenzoic acid 
• 7664-41-7 ammonia 
• 35112-28-8 methyl 2,4-dichlorobenzoate 
• 96385-49-8 4-chlorophthalamide 
• 34662-32-3 4-chloro-2-nitrobenzonitrile 
• 89-59-8 4-chloro-2-nitrotoluene 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 
• 74-11-3 para-chlorobenzoic acid 
• 5900-55-0 N-(5-chloro-2-methylphenyl)acetamide 
• 89-63-4 4-Chloro-2-nitroaniline 
• 2909-38-8 m-chlorophenyl isocyanate 

Downstream Products

• 40385-08-8 4-Chloro-2-(5-chloro-2-nitro-phenylamino)-benzoic acid 
• 41995-02-2 7-chloro-2-(4-chloro-2-nitro-phenyl)-benzo[d][1,3]oxazin-4-one 
• 89793-15-7 4-Chlor-N-sulfamoyl-anthranilsaeure 
• 79479-84-8 4-chloro-2<(tetrahydro-2-oxo-3-furanyl)amino>benzoic acid 
• 128615-75-8 10-Chloro-5-phenyl-6,6a,12-triaza-benzo[a]anthracen-7-one 
• 13165-16-7 7-chloro-2-thioxo-3-p-tolyl-2,3-dihydro-1H-quinazolin-4-one 
• 13165-15-6 7-chloro-3-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one 
• 31374-18-2 7-chloro-4-hydroxyquinazoline 
• 113290-36-1 methyl 4-chloro-2-(N,N-dimethyl-N'-formamidinyl)benzoate 
• 108608-00-0 4-Chloro-2-(3-phenyl-acryloylamino)-benzoic acid 
• 83389-06-4 acide chloro-4 isopropylamino-2 benzoique 
• 128615-79-2 10-Chloro-5-(4-chloro-phenyl)-6,6a,12-triaza-benzo[a]anthracen-7-one 
• 82256-07-3 6-methyl-2-(4-methylphenyl)-4(3H)-quinazolinone 
• 144459-78-9 4-Chloro-2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-benzoic acid 

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Provided herein are anti-fibrotic compounds, in particular those of Formula (I), that inhibit the TGF-beta signaling pathway. Also provided are pharmaceutical compositions comprising the anti-fibrotic compounds, and methods of treating diseases or conditions associated with fibrosis, inflammation, and benign or malignant neoplastic diseases in a subject by administering a compound or composition described herein. (Formula (I))