HCID 11448149, compound → 4-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one

HRID 1097772Notes

Reaction equation

HRID 1097772 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:17])([CH3:16])[CH:5]([OH:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.[H][H]>[Pd].CO>[OH:15][CH:5]1[C:6]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:12][C:3](=[O:2])[C:4]1([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 11448149HCID 11448149, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 592777124-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-oneYield 41.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-Hydroxy-2,2-dimethyl-3-(2-nitro-phenyl)-propionic acid methyl ester (800 mg), Palladium on carbon (10%, 80 mg) in 5 mL of MeOH under 1 atm hydrogen gas is stirred at room temperature for 4 h. The mixture is filtered through a pad of celite and washed with MeOH. The combined solution is concentrated and the residue is purified by flash column and gives 250 mg colorless solid.

Workup

  1. filtrationThe mixture is filtered through a pad of celite
  2. washwashed with MeOH
  3. concentrationThe combined solution is concentrated
  4. customthe residue is purified by flash column

Sources & evidence

ORD record
ord-2fa0650fc57749b9a3de03bd9f953c94
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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