9-Nitro-5,6-dihydro-benzo[f]quinoline → 9-Amino-5,6-dihydro-benzo[f]quinoline

HRID 521002Notes

Reaction equation

HRID 521002 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:16][CH2:15][C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]=2[CH:17]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[CH2:16][CH2:15][C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]=2[CH:17]=1

Participants

4

Reactant 1

HCID 582946079-Nitro-5,6-dihydro-benzo[f]quinoline

Product 1

HCID 582945549-Amino-5,6-dihydro-benzo[f]quinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 9-nitro-5,6-dihydro-benzo[f]quinoline (1.90 g), 10% palladium on carbon (0.20 g), and methanol (10 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 3 h. The catalyst is then separated by filtration and the filtrate is concentrated to give an oil that is submitted to the next reaction without further purification. Yield: 1.67 g (crude); Mass spectrum (ESI+): m/z=197 [M+H]+.

Workup

  1. customThe catalyst is then separated by filtration
  2. concentrationthe filtrate is concentrated
  3. customto give an oil that
  4. customis submitted to the next reaction without further purification

Sources & evidence

ORD record
ord-1860cece45ed4101ad0a6eec5f174ffc
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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