Potassium Carbonate → 6-methoxy-3-(trifluoromethyl)quinolin-2(1H)-one

HRID 55841Notes

Reaction equation

HRID 55841 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH:15]=O)=[O:5].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:14][O:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[NH:6][C:4](=[O:5])[C:3]([C:2]([F:18])([F:17])[F:1])=[CH:15]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 866899383,3,3-trifluoro-N-(2-formyl-4-methoxyphenyl)propanamide

Product 1

HCID 669801226-methoxy-3-(trifluoromethyl)quinolin-2(1H)-oneYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,3,3-trifluoro-N-(2-formyl-4-methoxyphenyl)propanamide (5.30 g, 20.3 mmol) in DMF (100 mL) was added K2CO3 (14.0 g, 101 mmol). The mixture was heated to 60° C. for 1.5 hours. The mixture was diluted with EtOAc (200 mL) and filtered off. The filtrate was washed with H2O (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo to give the desired product (4.60 g, yield 94%). 1H NMR (CDCl3 300 MHz): δ 12.25 (brs, 1H), 8.18 (s, 1H), 7.40 (d, J=9.0 Hz, 1H), 7.25 (dd, J=9.0, 2.7 Hz, 1H), 7.02 (d, J=2.7 Hz, 1H), 3.87 (s, 3H).

Workup

  1. filtrationfiltered off
  2. washThe filtrate was washed with H2O (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39e6cd15e59d4ad190ac693e34580017
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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