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

pka

1.51±0.10(Predicted)

color 

Pale lemon/gold

InChI

InChI=1S/C8H8ClNO2/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4H,10H2,1H3

InChIKey

LOCJPOYKBUUVKU-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(Cl)C(N)=C1

CAS DataBase Reference

40872-87-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HS Code 

2916399090

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

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