Methanol → 5-Amino-1,2-dihydroquinolin-2-one

HRID 420620

Reaction equation

HRID 420620 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:14])[NH:9]2)([O-])=O.CO.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:14])[NH:9]2

Participants

6

Reactant 3

HCID 887MethanolHCID 2437765-Nitro-1,2-dihydroquinolin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 157190785-Amino-1,2-dihydroquinolin-2-oneYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4.5 g of 5-nitroquinolin-2(1H)-one (Chem. Pharm. Bull., 29, 651 (1981)) is hydrogenated in 200 ml of ethyl acetate and 500 ml of methanol in the presence of 450 mg of palladium on activated carbon as a catalyst under normal pressure with hydrogen until the reaction is completed. The catalyst is removed by filtration through diatomaceous earth, and the reaction solution is concentrated by evaporation in a vacuum. 3.8 g of the title compound is obtained as a yellow solid.

Workup

  1. customThe catalyst is removed by filtration through diatomaceous earth
  2. concentrationthe reaction solution is concentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-9a77856c67614cb68cbd1c4187a002ae
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Linked notes

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