Hydrochloric Acid → HCID 21463196, compound

HRID 1940968Notes

Reaction equation

HRID 1940968 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][C:5]2([CH3:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].[CH3:22]I.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:22])[C:7](=[O:12])[CH2:6][C:5]2([CH3:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21463156HCID 21463156, compound

Product 1

HCID 21463196HCID 21463196, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-1,2,3,4-tetrahydro-4-methyl-2-oxo-4-phenylquinoline (6.0 g) in DMF (50 ml) was added sodium hydride (60% in oil) (0.98 g), followed by stirring at room temperature for 30 minutes. After this mixture was cooled to 0° C., methyl iodide (3 ml) was added, followed by stirring at room temperature for further 30 minutes. After dilute hydrochloric acid was added, the mixture was extracted with ethyl acetate. The extract was washed with water and then dried, after which the solvent was distilled off, to yield 6-chloro-1,2,3,4-tetrahydro-1,4-dimethyl-2-oxo-4-phenylquinoline as colorless crystals (5.58 g).

Workup

  1. temperatureAfter this mixture was cooled to 0° C.
  2. stirringby stirring at room temperature for further 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-d0c21a2a2a5c4545a1fa7f117d61b944
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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