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Sodium triacetoxyborohydride (3.47 g, 16.39 mmol) was added to a solution of methyl 4-amino-3-chlorobenzoate (1.014 g, 5.46 mmol), cyclopropanecarboxaldehyde (0.816 mL, 10.93 mmol), and acetic acid (1.876 mL, 32.78 mmol) in CH2Cl2 (40 mL). The reaction mixture was stirred at room temperature under nitrogen for 24 h. After concentration, the product was taken up with EtOAc (100 mL), washed with saturated NaHCO3 (3*20 mL), NaCl (20 mL) and dried over Na2SO4. The crude product was purified by MPLC on silica gel using Hex/EtOAc (4:1) to give 1.154 g (88%) of a colorless oil. 1H NMR (400 MHz, CHLOROFORM-D) delta 0.27-0.32 (m, 2H), 0.59-0.65 (m, 2H), 1.09-1.21 (m, 1H), 3.07 (dd, J=7.03, 5.08 Hz, 2H), 3.86 (s, 3H), 4.82-4.95 (m, 1H), 6.59 (d, J=8.59 Hz, 1H), 7.82 (dd, J=8.59, 1.95 Hz, 1H), 7.95 (d, J=1.95 Hz, 1H); MS (ESI) (M+H)+: 240.13.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-amino-3-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2009/62251; (2009); A1;,
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