Benzoic acid, 2-amino-3-chloro-, methyl ester → (2-Amino-3-chlorophenyl)methanol

Participants

Reaction Steps

A solution of methyl 2-amino-3-chlorobenzoate (1.7 g, 9.16 mmol) in THF (40 mL) was dropwise added to a suspension of the LAH (521 mg, 13.7 mmol) in THF (15 mL) at room temperature over 10 min under N2, and stirred for 2 hrs. The reaction was carefully quenched with saturated Na2SO4 (10 mL) at 0° C., extracted with Et2O (2×50 mL). The combined organic layers were washes with brine (30 mL), dried on MgSO4, and concentrated on rotary vacuum to afford the expected product as a yellow solid (1.08 g, 75%), which was pure enough to be used in the next step without further purification; 1H NMR (400 MHz, CDCl3), δ ppm 1.65 (s, 1 H), 4.59-4.70 (m, 4 H), 6.60-6.65 (m, 1 H), 6.96 (dd, J=7.55, 1.26 Hz, 1 H), 7.19-7.25 (m, 1 H); Mass spec. 158.02 (MH+), Calc. for C7H8ClNO2 157.03.

Provenance & Evidence