4-Methylcinnoline → 2-(1-aminopropan-2-yl)aniline
Reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1>CO.[Ni]>[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[CH:2]([CH3:1])[CH2:3][NH2:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Reduction of 4-methyl-cinnoline (10 g, 69.5 mmol) in methanol (100 mL), using Raney nickel (3 g). The catalyst was removed and washed with methanol. The filtrate was treated with an excess of HCl in isopropanol; ether was then added and the solution cooled. The precipitate was filtered and dried; 9.4 g (60%).
Workup
- customThe catalyst was removed
- washwashed with methanol
- additionThe filtrate was treated with an excess of HCl in isopropanol
- additionether was then added
- temperaturethe solution cooled
- filtrationThe precipitate was filtered
- customdried
Sources & evidence
- ORD record
- ord-f5ea5606d1254eb3a8970a90b37e595f
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300501B1
Reaction notes
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