Ethyl Acetate → HCID 136348361, compound

HRID 1922153Notes

Reaction equation

HRID 1922153 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]([CH3:14])=[CH2:13])[C:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)=[C:7]([CH3:27])[C:6]=2[C:5]([OH:28])=[CH:4][CH:3]=1.C(OCC)(=O)C>[OH-].[Pd+2].[OH-].CO>[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([CH:12]([CH3:13])[CH3:14])[C:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)=[C:7]([CH3:27])[C:6]=2[C:5]([OH:28])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 136348362HCID 136348362, compound

Product 1

HCID 136348361HCID 136348361, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8-chloro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol (0.26 g), ethyl acetate (10 mL), methanol (5.0 mL) and palladium hydroxide (0.05 g) was stirred at room temperature for 27 hours under an atmosphere of hydrogen. The mixture was filtered through Celite and the filtrated concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume) gave title compound as a yellow oil (0.21 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrated concentrated under reduced pressure
  3. customPurification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume)

Sources & evidence

ORD record
ord-046c372ee1084912bbcbad20caad4812
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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