[2-Nitro-4-(3-nitro-phenoxy)-phenyl]-acetic acid ethyl ester → 6-(3-Amino-phenoxy)-1,3-dihydro-indol-2-one

HRID 422035Notes

Reaction equation

HRID 422035 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)=[CH:8][C:7]=1[N+:22]([O-])=O)C>C(O)(=O)C.[Pd]>[NH2:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[O:12][C:9]1[CH:8]=[C:7]2[C:6]([CH2:5][C:4](=[O:3])[NH:22]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 59804301[2-Nitro-4-(3-nitro-phenoxy)-phenyl]-acetic acid ethyl ester

Product 1

HCID 598043186-(3-Amino-phenoxy)-1,3-dihydro-indol-2-oneYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of [2-nitro-4-(3-nitro-phenoxy)-phenyl]-acetic acid ethyl ester (496 mg, 1.4 mmol) in acetic acid (5 mL) is added 10% Pd/C (48 mg). The mixture is stirred under hydrogen (balloon) overnight. The catalyst is filtered off and the solvent is evaporated to dryness. The crude product is purified by column chromatography (EtOAc/Hexane=9:1) to give 120 mg of the desired product (yield 50%). LC/MS: 242.2 (MH+).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is evaporated to dryness
  3. customThe crude product is purified by column chromatography (EtOAc/Hexane=9:1)

Sources & evidence

ORD record
ord-a4a960d0622f425780203534ede8908c
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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