Methyl 2-(4-cyano-2-nitrophenyl)acetate → 2-Oxindole-6-carbonitrile

HRID 2244615Notes

Reaction equation

HRID 2244615 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](OC)=[O:11])=[C:5]([N+:14]([O-])=O)[CH:4]=1)#[N:2]>CC(O)=O.[Fe]>[O:11]=[C:10]1[CH2:9][C:6]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[NH:14]1

Participants

4

Reactant 1

HCID 23076960Methyl 2-(4-cyano-2-nitrophenyl)acetate

Product 1

HCID 27733482-Oxindole-6-carbonitrileYield 56.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Methyl (4-cyano-2-nitrophenyl)acetate (128 mg) was dissolved in AcOH (3.0 ml), followed by addition of iron powders (129 mg), and the reaction solution was stirred in an oil bath at 100° C. for 1.5 hours. It was concentrated to remove AcOH, followed by addition of EtOAc. The brown solid was separated by filtration, and the organic layer was washed with a 1M HCl solution and saturated brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (chloroform:CH3OH=99:1 to 95:5) to obtain to obtain 2-oxoindoline-6-carbonitrile (52.0 mg) as a pale yellow solid.

Workup

  1. concentrationIt was concentrated
  2. customto remove AcOH
  3. additionfollowed by addition of EtOAc
  4. customThe brown solid was separated by filtration
  5. washthe organic layer was washed with a 1M HCl solution and saturated brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=99:1 to 95:5)
  9. customto obtain

Sources & evidence

ORD record
ord-ea4d788918c74d4788b37444e00c1a11
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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