Dimethyl aminoterephthalate → Methyl 2-amino-4-(hydroxymethyl)benzoate

Participants

Reaction Steps

Methyl 2-amino-4-carbomethoxybenzoate (12, 4.0 g, 19.0 mmol) was dissolved in dry THF and cooled in a dry ice-acetone bath under an inert atmosphere. Super-hydride (65 mL, 1.0M) was added slowly by syringe over a period of 1 h. A small aliquot of the solution was quenched with water and purified on a silica gel column to yield methyl 2-amino-4-hydroxymethylbenzoate as a white solid: mp. 100°- 102° C. 1H NMR (CDCl3) δ 3.82 (s, 3 H, CH3), 4.64 (s, 2 H, CH2), 5.82 (br s, 2 H, NH2), 6.58 (d, J=8.1 Hz, 1 H), 6.66 (br s, 1 H), 7.81 (d, J=8.0 Hz, 1 H); MS (CI/NH3) m/e 182 (MH+, base), 167, 150.

Provenance & Evidence