Ethanol → HCID 12802695, compound

HRID 1448834Notes

Reaction equation

HRID 1448834 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](CC#N)=[CH:11][C:10]2=[O:22])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28]>>[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH2:28][C:27]([OH:25])=[O:29])=[CH:11][C:10]2=[O:22])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 12802694{1-[(4-Nitrophenyl)methyl]-2-oxo-1,2-dihydroquinolin-4-yl}acetonitrile

Product 1

HCID 12802695HCID 12802695, compound

Procedure

1-(4-Nitrobenzyl)-1,2-dihydro-2-oxoquinol-4-ylacetonitrile (0.5 g.) was added to a solution of sodium hydroxide (0.2 g.) in ethanol (50 ml.) and the mixture was heated under reflux for 5 hours. The ethanol was evaporated under reduced pressure and the residue was treated with 2 N hydrochloric acid (100 ml.). The precipitate thus formed was separated off and recrystallised from ethanol to give 1-(4-nitrobenzyl)-1,2-dihydro-2-oxoquinol-4-ylacetic acid (0.42 g.) m.p. 208°-210° C., (decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customThe ethanol was evaporated under reduced pressure
  4. additionthe residue was treated with 2 N hydrochloric acid (100 ml.)
  5. customThe precipitate thus formed
  6. customwas separated off
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-e730387c156a4bca84986b35046532a0
Source dataset
uspto-grants-1980_02
Patent number
US04187310

Reaction notes

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