Ethanol → HCID 67017335, compound

HRID 1842044Notes

Reaction equation

HRID 1842044 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[CH:9]=2)[N:4]([S:22]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27](F)[CH:26]=2)(=[O:24])=[O:23])[CH2:3]1.[CH2:35]([OH:37])[CH3:36].[H-].[Na+].O>CN(C)C=O>[CH3:34][C:2]1([CH3:1])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[CH:9]=2)[N:4]([S:22]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([O:37][CH2:35][CH3:36])[CH:26]=2)(=[O:24])=[O:23])[CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24758Sodium hydrideHCID 67017324HCID 67017324, compound

Product 1

HCID 67017335HCID 67017335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

165 mg 4-[3,3-Dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinoline-1-sulfonyl]-2-fluoro-benzonitrile and 30 ml ethanol were dissolved in 3 ml dimethylformamide. Then 10 mg sodium hydride were added and the reaction mixture stirred at room temperature for 4 hours. The mixture was then poured into 20 ml water and extracted five times with portions of 20 ml ethyl acetate. The combined organic extracts were dried over MgSO4 then evaporated in vacuo and the residue purified by chromatography on silica gel to obtain 40 mg 4-[3,3-Dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinoline-1-sulfonyl]-2-ethoxy-benzonitrile.

Workup

  1. extractionextracted five times with portions of 20 ml ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customthen evaporated in vacuo
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b5151df2c5fb489a85d661da40db3d85
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

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