Water → 1-methyl-3-formyl-4-hydroxy-2(1H)-quinolinone

HRID 36044Notes

Reaction equation

HRID 36044 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4](=[CH:13]N(C)C)[C:3]1=[O:17].[OH2:18]>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([CH:13]=[O:18])[C:3]1=[O:17]

Participants

3

Reactant 2

HCID 962WaterHCID 536541001-methyl-3-dimethylaminomethylene-(1H)-quinolin-2,4-dione

Product 1

HCID 1354542351-methyl-3-formyl-4-hydroxy-2(1H)-quinolinone

Procedure

The product from Step (1) was dissolved in distilled water (50 ml) by gentle warming and then the resulting solution was filtered. The clear filtrate was cooled in an ice bath and acidified to pH3 with mineral acid. The resulting crystalline precipitate was washed with water and dried to give 1 -methyl-3-formyl-4-hydroxy-2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data. MS: m/e 203 (M+); NMR (CDCl3): δ3.6 (s, 3H, NCH3), 10.28 (s, 1H, CHO) ppm.

Workup

  1. temperatureby gentle warming
  2. filtrationthe resulting solution was filtered
  3. temperatureThe clear filtrate was cooled in an ice bath
  4. washThe resulting crystalline precipitate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-11a1a58d1f9c4901a4a66cbb51ae2f0a
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

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