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

HRID 1935622Notes

Reaction equation

HRID 1935622 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].O1CCCC1>[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

5

Reactant 2

HCID 702EthanolHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-nitro-1H-indole-2-carboxylate (15.0 g, 0.0641 mol), 10% palladium-on-carbon catalyst, ethanol (300 ml) and tetrahydrofuran (300 ml) is hydrogenated at an initial pressure of 47 p.s.i. for 9 h and filtered through celite. The filtrate is concentrated and the residue is digested with hot diethyl ether. Concentration of the ether extract gave the titled product (11.14 g): MS (ES) m/z 205 (M+H+), 227 (M+Na+). *Uhlig, F.; Snyder, H. R. Adv. Org. Chem. 1960, 1, 35; Parmerter, S. M.; Cook, A. G.; Dixon, W. B. J. Am. Chem. Soc. 1958, 80, 4621-2.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate is concentrated
  3. extractionConcentration of the ether extract

Sources & evidence

ORD record
ord-778d1cbb352a468d8305644d7162e7f4
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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