Isopropyl iodide → HCID 54291364, compound

HRID 374998Notes

Reaction equation

HRID 374998 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[NH:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])=[CH:13][C:12]([CH3:23])=[C:11]([CH3:24])[CH:10]=2)=[O:5])[CH3:2].[H-].[Na+].[CH:28](I)([CH3:30])[CH3:29].C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:25][CH:28]([CH3:30])[CH3:29])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])=[CH:13][C:12]([CH3:23])=[C:11]([CH3:24])[CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 53649504HCID 53649504, compound

Product 1

HCID 54291364HCID 54291364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-chlorophenyl)-1,2-dihydro-6,7-dimethyl-2-oxo-3-quinolinecarboxylic acid ethyl ester (2.0 g) in DMF (20 ml) was added sodium hydride (60% in oil) (270 mg), followed by stirring at room temperature for 30 minutes. To this solution was added isopropyl iodide (0.9 ml), followed by stirring at 70° C. for 5 hours. After the mixture was cooled, ethyl acetate was added, and this mixture was washed successively with dilute hydrochloric acid, aqueous potassium carbonate and water and then dried, after which the solvent was distilled off. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=5:1), to yield 4-(2-chlorophenyl)-6,7-dimethyl-2-(1-methylethyloxy)-3-quinolinecarboxylic acid ethyl ester as colorless crystals (1.72 g).

Workup

  1. stirringby stirring at 70° C. for 5 hours
  2. temperatureAfter the mixture was cooled
  3. washthis mixture was washed successively with dilute hydrochloric acid, aqueous potassium carbonate and water
  4. customdried
  5. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-9ad4f4a62a2e4614b95796147882e2c7
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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