(-)-Ethyl (3-methyl-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 551004Notes

Reaction equation

HRID 551004 reaction equation
C[C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[NH:4][C:3]1=[O:14]>CO.[Pd]>[NH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:2]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:3](=[O:14])[NH:4]2

Participants

4

Reactant 1

HCID 86629726(-)-Ethyl (3-methyl-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 (3-methyl-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-d09f78ec449b4cf19ff67c0c411f148d
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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