反应详情

A solution of 2-amino-4-chlorobenzoic acid (10 g, 0.06 mol) in anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) was cooled to 0° C. in a 300 mL 3-necked flask fitted with a magnetic stirring bar and a constant additional funnel. Bromoacetyl bromide was added dropwise over a 2 h period while maintaining the internal temperature between 0°-2° C. After the addition was completed, the ice-water bath was removed, and then the reaction mixture was stirred 20 h. The reaction mixture was cooled in an ice-bath, water (300 mL) was slowly added, and then the white crystalline product which formed was filtered. Recrystallization from EtOAc/hexane gave 9.2 g (54%) of the title compound as a white solid: mp 156.4°-158° C.; 1H NMR (DMSO-d6) δ13.99 (s, 1H, NH), 11.72 (s, 1H, COOH), 8.54 (d, 1H, J=2.0), 8.00 (d, 1H, J=8.8), 7.27 (dd, 1H, J=2.4, J=6.4), 4.28 (s, 2H); 13C NMR (DMSO-d6) δ168.60, 165.54, 141.12, 138.51, 133.88, 123.36, 119.23, 115.58, 30.54; MS (EI, m/z) 293 (M+).

1. customfitted with a magnetic stirring bar and a constant additional funnel
2. temperaturewhile maintaining the internal temperature between 0°-2° C
3. additionAfter the addition
4. customthe ice-water bath was removed
5. temperatureThe reaction mixture was cooled in an ice-bath
6. additionwater (300 mL) was slowly added
7. customthe white crystalline product which formed
8. filtrationwas filtered
9. customRecrystallization from EtOAc/hexane