Sodium hydride → Ethyl 2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetate

HRID 1519917Notes

Reaction equation

HRID 1519917 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[CH:6]2.[H-].[Na+].CN(C=[O:22])C.[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>C1COCC1>[O:13]=[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[N:9]1[CH2:24][C:25]([O:26][CH2:27][CH3:23])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 337462666-(Trifluoromethyl)quinolin-2(1H)-one

Product 1

HCID 68783740Ethyl 2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring mixture of the above crude 6-(trifluoromethyl)quinolin-2(1H)-one in DMF/THF (0.5 M, 1:1) at rt was added NaH portionwise (1.2 g, 30.88 mmol) over 15 min. The reaction mixture was stirred at rt for additional 20 min before a solution of bromo methyl acetate (4.73 g, 30.88 mmol) in THF was added. The resulting mixture was stirred at rt until the starting material was consumed. The mixture was slowly quenched with brine and extracted with EtOAc. The crude product mixture was purified by column chromatography (3.6 g, 82% in two steps). Retention time (min)=2.042, method [1], MS(ESI) 286.1 (M+H).

Workup

  1. additionwas added
  2. customwas consumed
  3. customThe mixture was slowly quenched with brine
  4. extractionextracted with EtOAc
  5. customThe crude product mixture was purified by column chromatography (3.6 g, 82% in two steps)

Sources & evidence

ORD record
ord-7172d3caf7984972b588ea7f6349502a
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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