Lithium Hydroxide → 3-[(2,4-dichlorophenyl)methylamino]-5-phenyl-thiophene-2-carboxylic Acid

Participants

Reaction Conditions

Reaction Steps

3-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (70 mg, 0.18 mmol) was dissolved in a mixture of THF-MeOH—H2O (3:2:1) (20 mL) and then 1080 ul of LiOH 1N was added to it. After 16 h of stirring at temperature of 100° C., solvents were removed and then partitioned between 10 ml of H2O, 2 ml of KHSO4 5% and 10 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×10 mL). The combined ethyl acetate layer was dried (MgSO4) and concentrated to obtain 43 mg (63%) of 3-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid 1H-NMR (DMSO, 400 MHz): δ 7.65 ppm (m, 3H, Haro); 7.43-7.32 ppm (m, 5H, Haro); 7.23 ppm (s, 1H, Haro); 4.61 ppm (d, 2H, N—CH2).

Provenance & Evidence