Hydrochloric Acid → (6-Ethoxypyridin-3-yl)methanamine
Reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][N:5]=1)[CH3:2].Cl>C1COCC1>[NH2:9][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([O:3][CH2:1][CH3:2])=[N:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Add a solution of 1M BH3-THF complex in THF (7 mL, 7 mmol) to a solution of 6-(ethoxy)nicotinonitrile (911 mg, 4.41 mmol) in anhydrous THF (7 mL) and stir the mixture overnight at reflux. Add a second aliquot of 1M BH3-THF complex in THF (7 mL, 7 mmol) and stir the mixture overnight at reflux. Add 5N aqueous HCl (10 mL) cautiously and stir the mixture overnight at room temperature. Concentrate in vacuo then dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (250 mg, 40%). MS (ES+) m/z: 153 (M+H)+.