Hydrochloric Acid → 7-hydroxy-7-(3-nitrophenyl)-7H-furo[3,4-b]pyridin-5-one

HRID 861969Notes

Reaction equation

HRID 861969 reaction equation
[OH:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])N1CCCC.Cl.[OH2:26]>>[OH:26][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[O:1]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water2×HCID 197008597-Hydroxy-7-(3-nitrophenyl)-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one

Product 1

HCID 197008147-hydroxy-7-(3-nitrophenyl)-7H-furo[3,4-b]pyridin-5-one

Procedure

The 7-hydroxy-7-(3-nitrophenyl)-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one was mixed with 500 mL of water and 250 mL of concentrated hydrochloric acid was added. The mixture was heated under reflux for 20 hours. After cooling the mixture was diluted with 500 mL of water and the solid was removed by filtration. After washing the solid with water (500 mL) and methanol (200 mL) the material was dried to give 39.85 of 7-hydroxy-7-(3-nitrophenyl)-7H-furo[3,4-b]pyridin-5-one.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 20 hours
  4. temperatureAfter cooling the mixture
  5. customthe solid was removed by filtration
  6. washAfter washing the solid with water (500 mL) and methanol (200 mL) the material
  7. customwas dried

Sources & evidence

ORD record
ord-8f9160c9bc3f448686ef3f294d2394a4
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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