HCID 69960253, compound → HCID 18919039, compound

HRID 1291405Notes

Reaction equation

HRID 1291405 reaction equation
C([O:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]3[N:28]([CH3:29])[C:27](=[O:30])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]=4[CH3:31])[N:20]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)(=O)C>C1COCC1.C(OCC)(=O)C.CO.[Pd]>[CH3:29][N:28]1[C:27](=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[CH3:31])[N:20]=[C:19]1[CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:33][CH:32]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 69960253HCID 69960253, compound

Product 1

HCID 18919039HCID 18919039, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19895526THF ethyl acetate methanolSolvent

Procedure

To a solution of 2-[2-[4-(4-acetoxybenzoyl)phenyl]vinyl]-3,5-dimethyl-4(3H)-quinazolinone (631 mg) in THF-ethyl acetate-methanol (1:1:1) (50 ml) was added 10% Pd/C (50% hydrous) (126 mg) and the mixture was stirred under hydrogen at room temperature for 2 hours. The catalyst was then filtered off and the filtrate was concentrated. After the residue was suspended in ethanol (10 ml), 1N-aqueous sodium hydroxide solution (2.9 ml) was added and the mixture was stirred at room temperature for 2 hours. This reaction mixture was concentrated and the residue was suspended in water (20 ml) and neutralized with 1N-hydrochloric acid (2.9 ml). The precipitate was collected by filtration, washed with water, and dried to provide 538 mg of white powder.

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated
  3. addition1N-aqueous sodium hydroxide solution (2.9 ml) was added
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. concentrationThis reaction mixture was concentrated
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-62f49d39a85b48f1aecc12a5a26a74d8
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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