Potassium Carbonate → 4-methyl-1-phenylquinolin-2(1h)-one

HRID 2257484Notes

Reaction equation

HRID 2257484 reaction equation
C=C1OC(=O)C1.[OH:7][C:8]1[CH:17]=[C:16]([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.C(=O)([O-])[O-].[K+].[K+].I[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>[Cu]>[CH3:18][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:8](=[O:7])[CH:17]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 12661DiketeneHCID 178429252HCID 178429252, compound

Product 1

HCID 2691834-methyl-1-phenylquinolin-2(1h)-oneYield 54.7%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

The synthetic precursor (1) is prepared either by an Ullmann coupling according to a literature procedure (Wawzonek, et al., J. HETEROCYCLIC CHEM., 25, 381 (1988)) or via the reaction of the corresponding diarylamine with diketene followed by acid cyclization (Elderfield, HETEROCYCLIC COMPOUNDS, Vol. 4, pp. 1-331, (1952)). Thus 10.0 g (62.9 mmoles) of 2-hydroxy-4-methylquinoline is heated at reflux with 24.0 g (377 mmoles) of copper powder, 8.68 g (62.9 mmoles) of potassium carbonate and 19.2 g (94 mmoles) of iodobenzene for 48 hours. The reaction is cooled to room temperature, partitioned between water and ethyl acetate, filtered, and the organic layer is dried over magnesium sulfate. The crude product is purified on a silica gel column, eluting with 1:1 ethyl acetate/hexanes to yield 8.1 g of the desired product.

Workup

  1. customThe synthetic precursor (1) is prepared either by an Ullmann coupling
  2. custompartitioned between water and ethyl acetate
  3. filtrationfiltered
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. customThe crude product is purified on a silica gel column
  6. washeluting with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3549a3e9ec0348d8b22b22d3785c192b
Source dataset
uspto-grants-1997_08
Patent number
US05658751

Reaction notes

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