Water → 1-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde

HRID 2254577Notes

Reaction equation

HRID 2254577 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1.[CH3:16]I.O>CN(C)C=O>[CH3:16][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:13]([CH:14]=[O:15])[C:4]1=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5893342-Hydroxyquinoline-3-carbaldehyde

Product 1

HCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (55% w/w suspension in oil; 0.268 g) was added portionwise to a stirred suspension of 1,2-dihydro-2-oxoquinoline-3-carbaldehyde (1 g) in dimethylformamide (10 ml) which had been cooled in an ice bath. The mixture was allowed to warm to ambient temperature and was then heated to 60° C. for 1 hour. The mixture was recooled in an ice bath and methyl iodide (0.41 ml) was added. Dimethylformamide (50 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was poured into water (50 ml) and extracted with methylene chloride (3×50 ml). The combined extracts were washed with water (50 ml) and evaporated. The residue was triturated under diethyl ether to give 1,2-dihydro-1-methyl-2-oxoquinoline-3-carbaldehyde as a pale yellow solid (0.81 g, 74%).

Workup

  1. temperaturehad been cooled in an ice bath
  2. temperaturewas then heated to 60° C. for 1 hour
  3. customThe mixture was recooled in an ice bath
  4. extractionextracted with methylene chloride (3×50 ml)
  5. washThe combined extracts were washed with water (50 ml)
  6. customevaporated
  7. customThe residue was triturated under diethyl ether

Sources & evidence

ORD record
ord-2ef8a2e85632493fad327702b98ecaae
Source dataset
uspto-grants-1993_08
Patent number
US05236919

Reaction notes

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