Sodium Hydroxide → HCID 18457823, compound

Participants

Reaction Steps

Methyl 6′-methyl-3′-[(propylamino)carbonyl]-1,1′-biphenyl-4-carboxylate (216 mg, 0.7 mmol) in methanol (4 ml) was mixed with aqueous sodium hydroxide (2N, 1 ml) and stirred at room temperature for 2 h. The methanol was evaporated, the reaction diluted with water (4 ml) and extracted with chloroform (2×5 ml). The aqueous was acidified with hydrochloric acid (2N, 2 ml) and extracted with chloroform (2×6 ml). Both sets of organic extracts were combined in methanol (4 ml) and stirred with aqueous sodium hydroxide (2N, 2 ml) for 3 h. The methanol was evaporated, the reaction diluted with water (4 ml) and washed with chloroform (2×5 ml). The aqueous was acidified with hydrochloric acid (2N, 2 ml) and extracted with chloroform (2×6 ml). The solvent was evaporated from the organic extracts to give 6′-methyl-3′-[(propylamino)carbonyl]-1,1′-biphenyl-4-carboxylic acid (121 mg). NMR: δH CDCl3 8.13, (2H, d), 7.69, (1H, dd), 7.62, (1H, d), 7.41, (2H, d), 7.35, (1H, d), 3.42, (2H, t), 2.30, (3H, s), 1.64, (2H, m), 0.99, (3H, t).

Provenance & Evidence