(+/-)-Ethyl (4-nitro-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate → (+/-)-Ethyl (4-amino-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

HRID 2426157Notes

Reaction equation

HRID 2426157 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[O:13])[NH:8]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[O:13])[NH:8]2

Participants

4

Reactant 1

HCID 57663774(+/-)-Ethyl (4-nitro-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

Product 1

HCID 86629728(+/-)-Ethyl (4-amino-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (±)-ethyl (4-nitro-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate from Step A (2.56 g, 9.69 mmol) and 10% Pd/C (500 mg) was stirred vigorously in MeOH (50 mL) under an atmosphere of hydrogen (ca. 1 atm). After 16 h, the mixture was filtered through a pad of Celite, washing with MeOH, and the filtrate was concentrated in vacuo to give the title compound. MS: m/z=235 (M+1).

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fdca38f1dafc436f9aaff03a1bcc3c51
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

Loading…