Ethyl 7-nitro-1H-indole-2-carboxylate → 1H-Indole-2-carboxylic acid, 7-amino-, ethyl ester

HRID 1874819Notes

Reaction equation

HRID 1874819 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2)([O-])=O>C(O)C.[Pt](=O)=O>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2

Participants

4

Reactant 1

HCID 250407Ethyl 7-nitro-1H-indole-2-carboxylate

Product 1

HCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl esterYield 528.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Platinum(IV) oxide (0.024 g, 0.107 mmol) was added to a suspension of ethyl 7-nitro-1H-indole-2-carboxylate (0.10 g, 0.30 mmol) in ethanol (20 mL) in a Fisher-Porter vessel. The mixture was evacuated and flushed with nitrogen three times, flushed with hydrogen (60 psi) and evacuated three times, then filled with hydrogen (60 psi). After 30 min, the reaction mixture was filtered through celite. The filtrate was concentrated and the residue was purified by column chromatography (hexane/EtOAc) to give the title compound (0.324 g, 74%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 9.60 (s, 1H), 7.22 (d, 1H), 7.19 (d, 1H), 6.94-7.03 (m, 1H), 6.66 (d, 1H), 4.43 (q, 2H), 1.44 (t, 3H). MS: m/z 205 (M+1).

Workup

  1. customThe mixture was evacuated
  2. customflushed with nitrogen three times
  3. customflushed with hydrogen (60 psi)
  4. customevacuated three times
  5. additionfilled with hydrogen (60 psi)
  6. filtrationthe reaction mixture was filtered through celite
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-a8f6ec24f800483090ffc2f5fa76827b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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