1-Butanol → Anthranilic acid, 5-chloro-, butyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)[NH2:6].C(=O)([O-])[O-].[K+].[K+].[CH2:19](O)[CH2:20][CH2:21]C>>[CH2:1]([O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)[NH2:6])[CH2:19][CH2:20][CH3:21]Participants
4
Procedure
186 parts of 5-chloroanthranilic acid methyl ester, 150 parts of n-butanol and 10 parts of potassium carbonate are refluxed for half an hour. The separated methanol is then distilled off over a column. Distillation is continued until the boiling point of n-butanol is reached, then after addition of 4 parts each of bleaching earth and of active charcoal the hot mixture is filtered and agitated with 100 parts of acetone and 200 parts of ice. The reaction lasts for about 6 hours. The precipitate is filtered off, washed with ice-cold water and dried in vacuo at room temperature. There are obtained 211 parts of 5-chloroanthranilic acid-n-butyl ester, melting point 37°-39° C. The yield is 93% of the theory.