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Methyl 3-amino-4-chlorobenzoate

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Methyl 3-amino-4-chlorobenzoate Basic information
Product Name:Methyl 3-amino-4-chlorobenzoate
Synonyms:METHYL 3-AMINO-4-CHLOROBENZOATE;METHYL, 4-CHLORO-3-AMINOBENZOATE;Amino chlorobenzoic acid methyl ester;Methyl 3-Amino-4-chlorobenzene;Benzoic acid, 3-aMino-4-chloro-, Methyl ester;Methyl 3-AMino-4-chlorobenzoate, 98.0%(GC&T;Intedanib Impurity 5;3-amino-4-chloro-2-methylbenzoate
CAS:40872-87-5
MF:C8H8ClNO2
MW:185.61
EINECS:
Product Categories:FINE Chemical & INTERMEDIATES;Aromatic Esters
Mol File:40872-87-5.mol
Methyl 3-amino-4-chlorobenzoate Structure
Methyl 3-amino-4-chlorobenzoate Chemical Properties
Melting point 83 °C
Boiling point 292.1±20.0 °C(Predicted)
density 1.311±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
form crystalline powder
pka1.51±0.10(Predicted)
color Pale lemon/gold
InChIInChI=1S/C8H8ClNO2/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4H,10H2,1H3
InChIKeyLOCJPOYKBUUVKU-UHFFFAOYSA-N
SMILESC(OC)(=O)C1=CC=C(Cl)C(N)=C1
CAS DataBase Reference40872-87-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
HS Code 2916399090
MSDS Information
Methyl 3-amino-4-chlorobenzoate Usage And Synthesis
Synthesis To a solution of 3-amino-4-chlorobenzoic acid (15.0 g, 88.0 mmol) in methanol (90.0 mL), thionyl chloride (13.0 mL) was added drop-wise at 0 °C. The resulting mixture was refluxed for 12h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water (150 mL) and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate (50 mL) and brine solution (50 mL) and dried over sodium sulfate. The organic layer was removed under a rotary evaporator to yield Methyl 3-amino-4-chlorobenzoate (15.0 g, 92.5 per cent) as an off-white solid. 1H NMR (400 MHz, CDC13) δ 3.88 (s, 3H), 4.26 (brs, 2H), 7.29 (d, J = 8.2 Hz, 1H), 7.34-7.37 (dd, J = 1.9, 8.2 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H).
References[1] Patent: WO2011/128251, 2011, A1. Location in patent: Page/Page column 201
[2] Patent: US2011/257151, 2011, A1. Location in patent: Page/Page column 74
[3] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00708
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2465 - 2481
[5] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2051 - 2053
Methyl 3-amino-4-chlorobenzoate Preparation Products And Raw materials
Raw materials2-Amino-3-chlorobenzoic acid-->Methanol-->3-Amino-4-chlorobenzoic acid
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