6-Nitro-4-oxo-1-propionyl1,2,3,4-tetrahydroquinoline → 6-Amino-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 35676Notes

Reaction equation

HRID 35676 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:9][CH2:8][C:7]2=[O:18])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:9][CH2:8][C:7]2=[O:18]

Participants

4

Reactant 1

HCID 212947876-Nitro-4-oxo-1-propionyl1,2,3,4-tetrahydroquinoline

Product 1

HCID 212947846-Amino-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-nitro-4-oxo-1-propionyl1,2,3,4-tetrahydroquinoline (6.076 g) in methanol (60 ml) was hydrogenated over 5% palladium on carbon (0.5 g) under atmospheric pressure at ambient temperature. After the theoretical amount of hydrogen gas was absorbed, the catalyst was filtered off and the filtrate was evaporated in vacuo. The residual solid was washed with diethyl ether and dried to give 6amino-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (4.815 g).

Workup

  1. customAfter the theoretical amount of hydrogen gas was absorbed
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. washThe residual solid was washed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-0af32720cf964cb6b5c302da4faf5314
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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