1-(4-Nitrobenzoyl)-1,2,3,4-tetrahydroquinoline → (4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone

HRID 1291606Notes

Reaction equation

HRID 1291606 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 37636931-(4-Nitrobenzoyl)-1,2,3,4-tetrahydroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 2984117(4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanoneYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10% Pd--C (5 g) in ethanol (500 ml) is added 1-(4-nitrobenzoyl)-1,2,3,4-tetrahydroquinoline (53.4 g) and the mixture is subjected to catalytic reduction at ordinary temperature under atmospheric pressure of hydrogen. After the reduction, 10% Pd--C is removed by filtration, and the filtrate is concentrated under reduced pressure to give 1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (46.7 g) as yellow powder, m.p. 185°-188° C.

Workup

  1. customAfter the reduction, 10% Pd--C is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f8eb297d32cf49bdb3e8e15ac710971e
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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