2'-Methoxy-3-nitrobiphenyl-4-acetic acid → 6-(2-Methoxyphenyl)-1,3-dihydroindol-2-one

HRID 49128Notes

Reaction equation

HRID 49128 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[C:11]([N+:19]([O-])=O)[CH:10]=1>[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:12]([CH2:15][C:16](=[O:17])[NH:19]2)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 107796192'-Methoxy-3-nitrobiphenyl-4-acetic acid

Product 1

HCID 105619756-(2-Methoxyphenyl)-1,3-dihydroindol-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Iron chips (5 g) were added in one portion to 9.8 g of 2′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 hours. The reaction mixture was concentrated to dryness, sonicated in ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1N hydrochloric acid, water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel in ethyl acetate:hexane 1:2 to give 5.4 g (69 % yield based on-5-bromo-2-fluoronitrobenzene) of 6-(2-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 1N hydrochloric acid, water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel in ethyl acetate:hexane 1:2

Sources & evidence

ORD record
ord-0038a228dc874fd1a8eda843d293e4bf
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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