Acetic Acid → 1,3-Dihydro-5-(phenylthio)-2H-pyrrolo[2,3-c]pyridin-2-one

HRID 2394351Notes

Reaction equation

HRID 2394351 reaction equation
[N+:1]([C:4]1[C:5](CC(OC(C)(C)C)=O)=[N:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1)([O-])=O.[C:25](O)(=[O:27])[CH3:26]>[Fe]>[C:11]1([S:10][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][N:6]=2)[NH:1][C:25](=[O:27])[CH2:26]3)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 53869744HCID 53869744, compound

Product 1

HCID 189730441,3-Dihydro-5-(phenylthio)-2H-pyrrolo[2,3-c]pyridin-2-oneYield 77%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

A solution of t-butyl (3-nitro-6-phenylthio-2-pyridyl)acetate (1.04 g, 3.0 mmol) in glacial acetic acid containing iron powder (600 mg, 10.7 mmol) was heated at reflux for 5 hours. After cooling to room temperature, the mixture was poured into ice/water and extracted with chloroform. The combined chloroform extracts were washed with brine, dried (MgSO4) and concentrated to leave 5-phenylthio-6-azaoxindole as a light yellow solid (560 mg, 77%); m.p. 186°-189° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. extractionextracted with chloroform
  4. washThe combined chloroform extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c2bf6a195bc641bfb8dbdd5c4e02748d
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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