Imidazole → 6-Imidazol-1-yl-3,4-dihydro-1H-quinolin-2-one

HRID 1649745Notes

Reaction equation

HRID 1649745 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N:13]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 138852786-Imidazol-1-yl-3,4-dihydro-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.0 g of 6-bromo-3,4-dihydrocarbostyril, 300 mg of imidazole, 40 mg of cuprous iodide and 600 mg of potassium carbonate in 4 ml of N,N-dimethylformamide was heated at 90° C. for 48 hours. The reaction mixture was poured into water and extracted with a mixture of 10% methanol in methylene chloride. The organic layer was dried over anhydrous sodium sulfate, the solvent removed under reduced pressure and the residue chromatographed on silica gel, eluting with 3% methanol in methylene chloride, giving 6-(imidazol-1-yl)-3,4-dihydrocarbostyril, m.p. 205°-208° C.

Workup

  1. extractionextracted with a mixture of 10% methanol in methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customthe residue chromatographed on silica gel
  5. washeluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-e1cd7435ba1a45c49d74e9bd218d1344
Source dataset
uspto-grants-1990_05
Patent number
US04921862

Reaction notes

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