Ethanol → HCID 12802695, compound

HRID 1390297Notes

Reaction equation

HRID 1390297 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 (0.5g.) was added to a solution of sodium hydroxide (0.2g.) in ethanol (50ml.) and the mixture was heated under reflux for 5 hours. The ethanol was evaporated under reduced pressure and the residue was treated with 2N hydrochloric acid (100ml.). The precipitate thus formed was separated off and recrystallised from ethanol to give 1-(4-nitrobenzyl)-1,2-dihydro-2-oxoquinol-4-ylacetic acid (0.42g.) 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 2N hydrochloric acid (100ml.)
  5. customThe precipitate thus formed
  6. customwas separated off
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-e0f46148891b40bebdc300531284c8a2
Source dataset
uspto-grants-1979_02
Patent number
US04138490

Reaction notes

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