1-Butanol → Anthranilic acid, 5-chloro-, butyl ester

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.

1. distillationThe separated methanol is then distilled off over a column
2. distillationDistillation
3. additionafter addition of 4 parts
4. filtrationof active charcoal the hot mixture is filtered
5. filtrationThe precipitate is filtered off
6. washwashed with ice-cold water
7. customdried in vacuo at room temperature

ORD record

ord-c36bbca07b6848d8b66df8ad5925dcdb

Source dataset

uspto-grants-1979_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04135050