Methyl iodide → 1-methyl-6-nitro-4-trifluoromethyl-1H-quinolin-2-one
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[C:7]2[C:15]([F:18])([F:17])[F:16])([O-:3])=[O:2].[OH-].[K+].[CH3:21]I>>[CH3:21][N:10]1[C:11]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=2)[C:7]([C:15]([F:18])([F:16])[F:17])=[CH:8][C:9]1=[O:14]Participants
Procedure
6-Nitro-4-trifluoromethyl-1H-quinolin-2-one (2.50 g, 9.7 mmol) was methylated with KOH (5.46 g, 97.3 mmol) & MeI (6.1 mL, 97.3 mmol), as to give 1-methyl-6-nitro-4-trifluoromethyl-1H-quinolin-2-one (1.52 g, 57%): δH (CDCl3)=3.80 (s, 3H), 7.20 (s, 1H), 7.55 (d, 1H), 8.50 (dd, 1H), 8.75 (d, 1H). An EtOAc (50 mL) solution of this compound (1.26 g, 4.6 mmol) was treated with a slurry of Pd (10% on C, 95 mg, 0.09 mmol) in i-PrOH (2 mL). The mixture was stirred under a H2 atmosphere for 80 min, then more Pd (10% on C, 24 mg, 0.02 mmol) was added. After 20 min under H2, the mixture was filtered through Celite & the solvent removed to yield the title compound (1.06 g, 95%): δH (CDCl3)=3.70 (s, 3H), 3.75–3.85 (br s, 2H), 7.00–7.10 (m, 3H), 7.20 (d, 1H).
Sources & evidence
- ORD record
- ord-b4216f66d9d54bd8abacf998327fe60b
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074933B2
Reaction notes
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