Ethyl 4-nitro-1H-indole-2-carboxylate → HCID 12477537, compound

HRID 967113Notes

Reaction equation

HRID 967113 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:8]2)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:8]2

Participants

4

Reactant 1

HCID 283173Ethyl 4-nitro-1H-indole-2-carboxylate

Product 1

HCID 12477537HCID 12477537, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 4-nitroindole-2-carboxylate (2.3 g) and 10% palladium on carbon (0.5 g) in ethanol (400 ml) were stirred under a hydrogen atmosphere for 3 hours. The reaction was then filtered through Celite and concentrated to give the end product as a pale brown solid (1.4 g, 70%); NMR δ (CD3SOCD3) 1.3 (t, 3H), 4.3 (q, 2H), 5.4 (s, 2H), 6.1 (d, 1H), 6.6 (d, 1H), 6.9 (dd, 1H), 7.3 (s, 11H), 11.4 (bs, 1H); M/z (+) 205 (MH+).

Workup

  1. filtrationThe reaction was then filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4b943ced8414414d804bad54d98ddbc5
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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