(2-chloro-3-methylphenyl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Azidomethyl-2-chloro-3-methyl-benzene (2.99 g, 16.50 mmol) was dissolved in THF:H2O (3:1), triphenyl phosphine (4.40 g, 16.78 mmol) was added, followed by KOH (923 mg, 16.45 mmol) and the resulting mixture was stirred for 14 hours. The reaction mixture was then diluted with H2O, slowly acidified with HCl and the resulting aqueous layer was washed with Et2O (3×50 mL). The aqueous layer was then basified with NaOH (pH 14), extracted with Et2O (3×100 mL). The combined organic phases were washed with H2O (1×50 mL) and brine (1×50 mL), then dried over K2CO3 and concentrated to give the title amine. the resulting aqueous layer was washed with Et2O (3×50 mL) extracted with Et2O (3×100 mL) The combined organic phases were washed with H2O (1×50 mL) and brine (1×50 mL) dried over K2CO3 concentrated