1-Benzyl-5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-one → 5-(2,4-Dimethylphenyl)-3-methylcinnolin-4(1H)-one

HRID 598160Notes

Reaction equation

HRID 598160 reaction equation
C([N:8]1[C:17]2[C:12](=[C:13]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[CH3:25])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:26])[C:10]([CH3:27])=[N:9]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].Cl.C(O)C>[CH3:25][C:19]1[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=1[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[C:11](=[O:26])[C:10]([CH3:27])=[N:9][NH:8]2

Participants

6

Reactant 2

HCID 589386481-Benzyl-5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672672585-(2,4-Dimethylphenyl)-3-methylcinnolin-4(1H)-oneYield 52.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To 0.122 g (0.34 mmol) of 1-benzyl-5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-one and 0.14 g (0.10 mmol Pd) of 10% Pearlman's catalyst was added 4 mL of ethanol and two drops of concentrated HCl. The reaction vessel was charged with hydrogen via a balloon and stirred at room temperature for 3 h. The catalyst was removed by filtration, the filtrate was concentrated and the residue was purified by flash chromatography eluting with a 33% ethyl acetate/hexanes mixture to give 0.047 g (52%) of product as a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with a 33% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-dc24402b686646f48082b373143d57c2
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…