Aluminium lithium hydride → (4-Isopropylpyridin-2-yl)methanamine
Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]#[N:11])[CH:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][NH2:11])[CH:5]=1)([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of 149 mg (1.01 mmol) of 4-isopropylpicolinonitrile in 7 mL of THF at 0° C. was added 150 mg (3.95 mmol) of LiAlH4. After about 15 min., 250 mg of LiAlH4 was added, and after about 15 min. the ice bath was removed and stirring was continued with warming to r.t. After 40 min., 400 μL of H2O, 400 μL of 15% NaOH (aq), and 1.2 mL of brine were added in succession. The mixture was stirred for 85 min., filtered through Celite, and conc. to give 143 mg of (4-isopropylpyridin-2-yl)methanamine which was used without further purification.