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

HRID 1586070Notes

Reaction equation

HRID 1586070 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-cdb661e20c6346808c48d55969ad120c
Source dataset
uspto-grants-1999_08
Patent number
US05942522

Reaction notes

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