4-Amino-3-chloro-benzoic acid ethyl ester Chemical Properties

Melting point:

83-84°C

Boiling point:

110-115 °C(Press: 0.001 Torr)

Density 

1.262±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

0.56±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2922498590

4-Amino-3-chloro-benzoic acid ethyl ester Usage And Synthesis

Uses

4-Amino-3-chloro-benzoic acid ethyl ester is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

To a solution of ethyl 4-aminobenzoate (2.0 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (NCS, 2.05 mmol). The reaction mixture was heated to reflux for 5 hours. Upon completion of the reaction, the reaction mixture was extracted with ethyl acetate and the organic layer was washed with 5% sodium hydroxide solution and subsequently dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the crude product. Purification by recrystallization in hexane afforded ethyl 4-amino-3-chlorobenzoate (27c) as purple crystals (melting point 81-83 °C) in 86% yield. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3): 1H NMR δ 1.33 (t, 3H, J=7.0 Hz, CH3), 4.29 (q, 2H, J=7.0 Hz, CH2), 6.70 (d, 1H, J=8.5 Hz, Ar-H), 7.72 (dd , 1H, J=8.4,1.9 Hz, Ar-H), 7.92 (d, 1H, J=1.9 Hz, Ar-H); 13C NMR δ 14.30, 60.62, 114.35, 118.06, 120.63, 129.52, 131.12, 146.97, 165.74.

References

[1] Organic Letters, 2008, vol. 10, # 1, p. 113 - 116
[2] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 1, p. 109 - 124
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 27, p. 6973 - 6982
[4] Patent: US5502073, 1996, A
[5] Patent: US5516774, 1996, A

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