Hydrochloric Acid → 2-Chlorobenzylamine

Temperature

130 °C

A 250 mL, round-bottomed, 3-necked flask was charged with 82.5 g of 20% aqueous potassium hydroxide and 20 g (73.6 mmol) of 2-chlorobenzylphthalimide. The reaction mixture was refluxed (bath temperature 130° C.) for 18.3 h with stirring, and then allowed to cool to room temperature. A mixture containing 50 mL of water and 50 mL of concentrated hydrochloric acid was then added dropwise and the reaction mixture was heated under reflux for a further 22.5 hours. The reaction mixture was then allowed to cool, and the cooled reaction mixture was filtered, and the collected solids were washed with 5×10 mL of water, and dried in a vacuum oven. NMR, IR and GC analysis indicated these to be mainly phthalic acid contaminated with 2-chlorobenzylphthalamic acid (11.2 g, 92%). The filtrate was rendered basic (pH 10) by the addition of potassium hydroxide pellets, and was then extracted with 4×100 mL of methylene chloride. After stripping of the solvent, a 98% yield (10.23 g) of 2-chlorobenzylamine was obtained (purity 99% by GC).

1. temperatureto cool to room temperature
2. additionwas then added dropwise
3. temperaturethe reaction mixture was heated
4. temperatureunder reflux for a further 22.5 hours
5. temperatureto cool
6. customthe cooled reaction mixture
7. filtrationwas filtered
8. washthe collected solids were washed with 5×10 mL of water
9. customdried in a vacuum oven
10. additionby the addition of potassium hydroxide pellets
11. extractionwas then extracted with 4×100 mL of methylene chloride

ORD record

ord-bf187bb080c44704864c289a3a8c2e13

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04960938