Hydrochloric Acid → 2-Methyl-4-(trifluoromethoxy)benzylamine

Reaction equation

[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.Cl.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:13])([F:14])[F:15])[CH:8]=[CH:7][C:3]=1[CH2:4][NH2:6]

Participants

Procedure

18.8 ml (18.8 mmol) of borane-THF-complex (1M) are provided under argon and ice cooling. A solution of 823 mg (3.76 mmol) of 2-methyl-4-(trifluoromethoxy)benzamide (Example 68A) in 80 ml of THF is added dropwise and the reaction mixture is subsequently stirred for 8 h under reflux. Under ice cooling 80 ml of 1N hydrochloric acid are added dropwise (until the end of the evolution of gas) and the reaction mixture is heated for 1 h under reflux. The reaction mixture is subsequently adjusted to an alkaline pH with a 1N sodium hydroxide solution, extracted three times with dichloromethane and the combined organic phases are dried over sodium sulfate and the solvent is removed under vacuum. An oil is obtained which is reacted further without further purification. Yield: 732 mg (95% of theory).