Ethyl cyanoacetate → Ethyl 7-(cyano-ethoxycarbonyl-methyl)-6,8-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinoline-carboxylate

HRID 1032019Notes

Reaction equation

HRID 1032019 reaction equation
[H-].[Na+].O1CCOCC1.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].[F:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([F:29])[C:27]=1F)[N:24]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[CH:23]=[C:22]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:21]2=[O:42]>O>[C:9]([CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:27]1[C:26]([F:29])=[C:25]2[C:20]([C:21](=[O:42])[C:22]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:23][N:24]2[C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)=[CH:19][C:18]=1[F:17])#[N:10]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 13728329Ethyl 1-(4-fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylate

Product 1

HCID 14422917Ethyl 7-(cyano-ethoxycarbonyl-methyl)-6,8-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinoline-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.12 g of sodium hydride are initially introduced into 15 ml of dioxane. 0.51 g of ethyl cyanoacetate is added and the mixture is first stirred for one hour at room temperature. 1.1 g of ethyl 6,7,8-trifluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinoline-carboxylate are then added in portions. The mixture is boiled for 3 hours, diluted using water and acidified. It is extracted using methylene chloride.

Workup

  1. waitThe mixture is boiled for 3 hours
  2. additiondiluted
  3. extractionIt is extracted

Sources & evidence

ORD record
ord-35cf28b0dbc44a8bbdb3f60fe08ab392
Source dataset
uspto-grants-1990_09
Patent number
US04956465

Reaction notes

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