Sodium Hydroxide → 3-Chloro-4-pyrrolidinobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 3-chloro-4-(1-pyrrolidinyl)benzoate (D39) (685 mg, 2.71 mmol) and aqueous sodium hydroxide (2M, 1.36 mL, 2.72 mmol) in ethanol (15 mL) was heated at 40° C. for 17 h. Further sodium hydroxide (1.36 mL, 2.72 mmol) was added and the reaction heated for a further 8 h. The mixture was concentrated and the residue dissolved in water (100 mL). The aqueous phase was washed with ethyl acetate (2×100 mL) and then acidified to pH 6. A white solid formed and hence was filtered off, washed with water and dried in a vacuum oven to give the title compound as an off-white solid (362 mg). MS (ES): C11H1235ClNO2 requires 225; found 226 (MH+).

Provenance & Evidence