Aniline → 6-phenyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

HRID 749105Notes

Reaction equation

HRID 749105 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]([O:9][C:10](=[O:11])[C:2]=12)=O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[C:13]1([N:12]2[C:7](=[O:9])[C:3]3[C:2](=[N:1][CH:6]=[CH:5][CH:4]=3)[C:10]2=[O:11])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 69688Furo[3,4-b]pyridine-5,7-dione

Product 1

HCID 7048266-phenyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-pyridinedicarboxylic acid anhydride (19.4 g) in tetrahydrofuran (260 mL) was added aniline (11.8 mL) and the mixture was refluxed 2 hours. The reaction mixture was concentrated. Acetic anhydride (65 mL) was added to the reaction mixture, which was refluxed for 1.5 hours. After cooling in ice bath, the reaction mixture was poured in ice water (200 mL) and stirred for 1 hours. The precipitate was collected by filtration. It was washed with water and then washed with ethanol on heating to give the title compound (20.9 g) having the following physical data.

Workup

  1. temperaturethe mixture was refluxed 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionAcetic anhydride (65 mL) was added to the reaction mixture, which
  4. temperaturewas refluxed for 1.5 hours
  5. temperatureAfter cooling in ice bath
  6. additionthe reaction mixture was poured in ice water (200 mL)
  7. filtrationThe precipitate was collected by filtration
  8. washIt was washed with water
  9. washwashed with ethanol
  10. temperatureon heating

Sources & evidence

ORD record
ord-2705775fb1a84d11bb28ab16535cdb5b
Source dataset
uspto-grants-2008_07
Patent number
US07402580B2

Reaction notes

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