Potassium Hydroxide → HCID 58970765, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4{[(4-methyl-2-nitrophenyl)(2,2,2-trifluoroacetyl)-amino]methyl}benzoic acid methyl ester (14.0 g, 35 mmol) in CH2Cl2, was treated with tetrabutylammonium bromide (1.13 g, 3.5 mmol) and 20% aq. KOH (100 mL). The reaction mixture was heated to 38° C. for 3 h and cooled to room temperature. The phases were separated, the aqueous phase was extracted with CH2Cl2. The combined extracts and organic phase were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford 4-[(4-methyl-2-nitrophenylamino)methyl]-benzoic acid methyl ester as an orange solid. Yield: 90%. 1H NMR (400 MHz, CDCl3): 8.37 (bs, 1H); 8.02 (m, 3H); 7.40 (d, J=8 Hz, 2H); 7.19 (d, J=8 Hz, 1H); 6.63(d, J=8 Hz, 1H); 4.60(d, J=8 Hz, 2H); 3.91(s,3H); 2.35 (s, 1H).

Provenance & Evidence