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

HRID 552825

Reaction equation

HRID 552825 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-541b4f61fcf84ca78a21f45b4ff0231a
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Linked notes

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