Potassium Carbonate → 4-(3-Butyl-1,4-dihydro-4-oxo-quinolinyl methyl)-benzonitrile

HRID 1602933Notes

Reaction equation

HRID 1602933 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10].Br[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1>CC(C)=O>[CH2:7]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:1][C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH:12]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12162Benzonitrile, 4-bromo-HCID 195953413-butyl-4-(1H)-quinolinone

Product 1

HCID 196085034-(3-Butyl-1,4-dihydro-4-oxo-quinolinyl methyl)-benzonitrileYield 113.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.3 g of activated potassium carbonate were added to a suspension of 2.3 g of the product of Step E in 50 ml of acetone a the mixture was stirred for 10 minutes. Then, 4.7 g of 4-bromobenzonitrile were added, followed by heating for 4 hours at reflux. The acetone was evaporated off and the residue was taken up in 100 ml of water. Extraction was carried out with ethyl acetate and the extracts were washed with a saturated solution of ammonium chloride, dried and evaporated to dryness to obtain 4.1 g of the expected product which was chromatographed on silica (eluant: methylene chloride-methanol (98-2)) to obtain 3.3 g of the desired product melting at 168° C.

Workup

  1. temperatureby heating for 4 hours
  2. temperatureat reflux
  3. customThe acetone was evaporated off
  4. extractionExtraction
  5. washthe extracts were washed with a saturated solution of ammonium chloride
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-ed6aad7ef91740ed8914cefcfa7eeb73
Source dataset
uspto-grants-1999_11
Patent number
US05985894

Reaction notes

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