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

HRID 1869372

Reaction equation

HRID 1869372 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. (1981), 29, pp. 651-56) 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-75c3d875ab254ea4a461d78a402bba6f
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Linked notes

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