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>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 7-nitroquinoline (D54) (0.65 g, 3.71 mmol) and 10% palladium on charcoal (65 mg, 54% water) in methanol (20 ml) was hydrogenated at 1 atm. and ambient temperature for until complete by tlc. The catalyst was filtered off and washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the title compound as a brown solid (0.53 g). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.75 (dd, 1H), 7.98 (dd, 1H), 7.62 (d, 1H), 7.21 (d, 1H), 7.14 (dd, 1H), 6.99 (dd, 1H), 4.07 (br, 2H).
Workup
- customwas hydrogenated at 1 atm. and ambient temperature
- filtrationThe catalyst was filtered off
- washwashed with further methanol
- filtrationThe combined filtrated
- concentrationwashings were concentrated in vacuo
Sources & evidence
- ORD record
- ord-2aa36f04dfe5494f85b06189f667b4b3
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538121B2
Reaction notes
Loading…