1-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone → 1-(7-Amino-3,4-dihydro-4,4-dimethylquinolin-1(2h)-yl)ethanone

HRID 888099Notes

Reaction equation

HRID 888099 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[N:5]([C:15](=[O:17])[CH3:16])[CH2:4][CH2:3]1>CO.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH3:18])([CH3:1])[CH2:3][CH2:4][N:5]2[C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 590215001-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone

Product 1

HCID 590215121-(7-Amino-3,4-dihydro-4,4-dimethylquinolin-1(2h)-yl)ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of 1-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone (0.97 g) and Pd/C (10 wt %, 0.20 g) in 10 ml of MeOH was placed under H2 and stirred at RT for 2 h then filtered through a pad of Celite. Removal of the solvents gave 1-(7-amino-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone as an off-white viscous oil.

Workup

  1. filtrationthen filtered through a pad of Celite
  2. customRemoval of the solvents

Sources & evidence

ORD record
ord-e6b22e1185444228b859d2a62a85ecb2
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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