4'-Methoxy-3-nitrobiphenyl-4-acetic acid → 6-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-one

HRID 1937602Notes

Reaction equation

HRID 1937602 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[C:11]([N+:19]([O-])=O)[CH:10]=2)=[CH:5][CH:4]=1>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:12]([CH2:15][C:16](=[O:17])[NH:19]3)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 104935034'-Methoxy-3-nitrobiphenyl-4-acetic acid

Product 1

HCID 107286906-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-oneYield 54%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Iron chips (3.6 g) were added in one portion to 7.2 g 4′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL glacial acetic acid and heated at 100° C. overnight. The reaction mixture was concentrated to dryness, sonicated in ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1 N hydrochloric acid, then with brine, dried over anhydrous sodium sulfate and concentrated to give 2.7 g (54% yield based on 5-bromo-2-fluoronitrobenzene) of 6-(4-methoxyphenyl)-2-oxindole as a rose colored solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customsonicated in ethyl acetate
  3. filtrationfiltered
  4. customto remove the insolubles
  5. washThe filtrate was washed twice with 1 N hydrochloric acid
  6. dry with materialwith brine, dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e72d4570ab6945ea8b4859b54308d48a
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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