Sodium Hydroxide → 1-Benzyl-4-hydroxy-6-methylquinolin-2(1H)-one

HRID 1768528Notes

Reaction equation

HRID 1768528 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=2)[CH:11]=[C:10](C(OCC)=O)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[Na+]>>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=2)[C:11]([OH:25])=[CH:10][C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 152290011-benzyl-3-carbethoxy-6-methyl-2(1H)-quinolinone

Product 1

HCID 546928611-Benzyl-4-hydroxy-6-methylquinolin-2(1H)-one

Procedure

The product from Step (3) was dissolved in 2N sodium hydroxide (150 ml) and the solution was refluxed for 4 hours. Then the solution was cooled and acidified with mineral acid to pH3. The solid was filtered off, dried and crystallized from ethyl acetate/hexane to give 1-benzyl-4-hydroxy-6-methyl-2(1H)-quinolinone (4.0 gm). That the expected product was obtained was confirmed by the spectral data: MS: m/e 265 (M·+); NMR (DMSO): δ2.32 (s, 3H, CH3 -Ar), 5.43 (s, 2H, CH2 -Ar), 5.96 (s, 1H, =CH--), 11.48 (s, 1H, OH) ppm.

Workup

  1. temperaturethe solution was refluxed for 4 hours
  2. temperatureThen the solution was cooled
  3. filtrationThe solid was filtered off
  4. customdried
  5. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ca1b623c72a5415cbbb8846cc79ade38
Source dataset
uspto-grants-1995_01
Patent number
US05378694

Reaction notes

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