2-Chloroethanol → HCID 59601968, compound

Participants

Reaction Steps

A mixture of 15 g (84 mmol) of 4-(ethylamino)benzoic acid methyl ester, 15 mL (0.224 mol) of ethylene chlorohydrine and 14.5 mL (84 mmol) of diisopropyl ethyl amine was refluxed for 5 hours. During the reflux, the temperature rose from 105° C. to 140° C. The reaction mixture was allowed to cool down to room temperature and 100 mL of water and 250 mL of ethyl acetate was added. After extraction, the organic fraction was isolated, washed 3 times with 50 mL of water, once with 50 mL of brine and dried over MgSO4. The solvent was removed under reduced pressure and N-ethyl-N-(2-hydroxyethyl)-4-aminobenzoic acid methyl ester was isolated by preparative column chromatography on Kieselgel 60 (Aldrich) using cyclohexane/ethyl acetate 1/1 as eluent. 5.0 g of N-ethyl-N-(2-hydroxyethyl)-4-aminobenzoic acid methyl ester was isolated (m.p. 61-64° C.)

Provenance & Evidence