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

HRID 269721Notes

Reaction equation

HRID 269721 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].O.C([O-])=O.[NH4+]>[Pd].CO>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH2:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylateHCID 2723923Ammonium formate

Product 1

HCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

5 g of 5-nitro-1H-indole-2-carboxylic acid ethyl ester is introduced into 170 ml of methanol and 0.5 ml of water, mixed with 6.73 g of ammonium formate and with 50 mg of palladium on carbon (10%) and refluxed for 1 hour at 90° C. Then, it is suctioned off on Celite and rewashed with warm methanol. After the solvent is removed, the residue is mixed with 100 ml of water, stirred for 10 minutes, and the precipitated solid is suctioned off on a G4 frit. The thus obtained solid is dried in a vacuum. In this way, 4.12 g of the title compound is obtained.

Workup

  1. customAfter the solvent is removed
  2. additionthe residue is mixed with 100 ml of water
  3. customThe thus obtained solid is dried in a vacuum

Sources & evidence

ORD record
ord-00d12ba002bc4474b88cf9fb83bf38a6
Source dataset
uspto-grants-2008_11
Patent number
US07449459B2

Reaction notes

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