Acetic Acid → HCID 178470052, compound

HRID 1949160Notes

Reaction equation

HRID 1949160 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:24])[CH2:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=1[C:21](=O)[CH3:22])=[O:9])[CH3:4].CC(O)=O>CCO.O>[CH2:3]([O:5][C:6]([C:7]1[C:8]([OH:9])=[N:10][C:11]2[C:12]([C:21]=1[CH3:22])=[CH:13][CH:14]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:16]=2)=[O:24])[CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 68510474HCID 68510474, compound

Product 1

HCID 178470052HCID 178470052, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

30 mg (0.68 mmol, 60% in mineral oil) sodium hydride were added to a solution of 190 mg (0.62 mmol) 3-(2-acetyl-5-tert-butyl-phenylamino)-3-oxopropanoic acid ethyl ester in EtOH (2 ml) and the mixture was heated for 2 h at 80° C. Then it was diluted with water and acidified with 5N AcOH. It was then extracted with EE. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 150 mg (0.52 mmol, 84%) 7-tert-butyl-2-hydroxy-4-methyl-quinoline-3-carboxylic acid ethyl ester were obtained as the residue, which was reacted further with no additional purification.

Workup

  1. extractionIt was then extracted with EE
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-8fc6f856f780432ca3cc05c615c89f36
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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