Carbazole, 2-nitro- → 2-Aminocarbazole

HRID 1938375Notes

Reaction equation

HRID 1938375 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 99612Carbazole, 2-nitro-

Product 1

HCID 446192-Aminocarbazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Nitrocarbazole [Meridenhall, G. D.; Smith, P. A. S. Org. Syn. Coll. Vol. 5 1973, 829, the disclosure of which is herein incorporated by reference](structure 14 of Scheme IV, where R1 -6 =H, X=NH) (1.0 g, 4.7 mmol) in 50 mL of ethyl acetate was hydrogenated over 10% Pd/C (50 mg) under an atmosphere of hydrogen for 1.5 h at rt giving, after filtration through Celite™, 840 mg (100%) of 2-aminocarbazole. Data for 2-aminocarbazole: 1 H NMR (400 MHz, CDCl3) 7.94 (d, J=9.0, 1H), 7.83 (d, J=8.0, 1H), 7.80 (br s, 1H), 7.35 (m, 2H), 7.15 (dd, J=8.2, 1H), 6.67 (d, J=1.8, 1H), 6.58 (dd, J=9.0, 1.8, 1H), 3.73 (br s, 2H).

Workup

  1. customgiving
  2. filtrationafter filtration through Celite™, 840 mg (100%) of 2-aminocarbazole

Sources & evidence

ORD record
ord-b868feef818b4c0da43f98c7ea686bd4
Source dataset
uspto-grants-1997_12
Patent number
US05693646

Reaction notes

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