7-Nitroquinoline → 7-Aminoquinoline

HRID 494187Notes

Reaction equation

HRID 494187 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 119467-Nitroquinoline

Product 1

HCID 113777-AminoquinolineYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-nitroquinoline (D54) (0.65 g, 3.71 mmol) and 10% palladium on charcoal (65 mg, 54% water) in methanol (20 ml) was hydrogenated at 1 atm. and ambient temperature for until complete by tlc. The catalyst was filtered off and washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the title compound as a brown solid (0.53 g). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.75 (dd, 1H), 7.98 (dd, 1H), 7.62 (d, 1H), 7.21 (d, 1H), 7.14 (dd, 1H), 6.99 (dd, 1H), 4.07 (br, 2H).

Workup

  1. customwas hydrogenated at 1 atm. and ambient temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with further methanol
  4. filtrationThe combined filtrated
  5. concentrationwashings were concentrated in vacuo

Sources & evidence

ORD record
ord-2aa36f04dfe5494f85b06189f667b4b3
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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