7-Nitroquinoline → 7-Aminoquinoline
Reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 7-nitroquinoline (0.30 g, 0.0017 mol; Specs, Inc.), 10% Pd-C (50 mg), and MeOH (20 mL) was stirred under H2 (1 atm) for 2 h. The mixture was filtered and the filtrate was concentrated to give a yellow solid (235 mg, 95%). LC-MS: 0.33 min, 145.1 (M+1). 1H NMR (DMSO-d6): 8.58 (1H, dd, J=4.4, 1.6 Hz), 8.00 (1H, dd, J=8.0, 1.2 Hz), 7.60 (1H, d, J=8.8 Hz), 7.07 (1H, dd, J=8.0, 4.4 Hz), 6.98 (1H, dd, J=8.8, 2.0 Hz), 6.93 (1H, d, J=2.0 Hz), 5.75 (s, 2H).
Workup
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-cdab124919204f539fd1329a0ac3bc1d
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576099B2
Reaction notes
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