3-Ethoxymethyl-5-nitroisoquinoline → 5-Amino-3-ethoxymethylisoquinoline
Reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([N+:15]([O-])=O)[CH:11]=[CH:10][CH:9]=2)[CH3:2]>C(O)C.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]=[CH:7]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A catalyst (3% palladium-on-charcoal; 3.5 g) is added to a solution of 3-ethoxymethyl-5-nitroisoquinoline (24 g) in ethanol (350 cc). A stream of hydrogen is bubbled through for 4 hours, whilst keeping the temperature at about 25° C. with the aid of a bath of cold water. The suspension is filtered and the filtrate is evaporated to dryness at 50° C. under reduced pressure (20 mm Hg). The residue is recrystallised from diisopropyl ether (200 cc). 5-Amino-3-ethoxymethylisoquinoline (16.5 g), melting at 95° C., is obtained.