Ethyl 5-nitro-1H-indole-2-carboxylate → Ethyl 5-amino-1H-indole-2-carboxylate

HRID 1874816Notes

Reaction equation

HRID 1874816 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2

Participants

4

Reactant 1

HCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateYield 60.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of ethyl 5-nitro-1H-indole-2-carboxylate (0.100 g, 0.43 mmol) in 5 mL of absolute ethanol was added 5% palladium on carbon (0.045 g, 0.021 mmol). The mixture was evacuated and flushed with nitrogen, then filled with hydrogen at 50 psi. After 3 h, the reaction mixture was filtered through Celite and the filtrate was evaporated to give the title compound (0.053 g, 60%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.33 (s, 1H), 7.10 (d, 1H), 6.78 (d, 1H), 6.58-6.69 (m, 2H), 4.70 (br. s., 2H), 4.25 (q, 2H), 1.27 (t, 3H). MS: m/z 205 (M+1).

Workup

  1. customThe mixture was evacuated
  2. customflushed with nitrogen
  3. additionfilled with hydrogen at 50 psi
  4. filtrationthe reaction mixture was filtered through Celite
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-3ac1b6f67cb04f9589d694d85de9192b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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