Nitric Acid → 7-Hydroxy-7-(3-nitrophenyl)-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one

HRID 861968Notes

Reaction equation

HRID 861968 reaction equation
[OH:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH3:15].S(=O)(=O)(O)O.[N+:27]([O-])([OH:29])=[O:28]>O>[OH:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:27]([O-:29])=[O:28])[CH:17]=2)[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 197009447-Hydroxy-7-phenyl-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one

Product 1

HCID 197008597-Hydroxy-7-(3-nitrophenyl)-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-Hydroxy-7-phenyl-6-(n-butyl)-6,7-dihydropyrrolo-[3,4-b]pyridin-5-one (47.15 g, 167 moles) was mixed with 250 mL of concentrated sulfuric acid (96%). The resulting mixture was placed in a cooling bath. Nitric acid (70%, 12 mL, 189 moles) was added at such a rate that the temperature remained below 45° C. The mixture was stirred for 30 minutes poured onto ice (500 g) and diluted with 1 L of water. The mixture was extracted twice with 700 mL of ethyl acetate. The organic solvent was removed yielding 7-hydroxy-7-(3-nitrophenyl)-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]-pyridin-5-one, which was used without further purification.

Workup

  1. customThe resulting mixture was placed in a cooling bath
  2. customremained below 45° C
  3. additionpoured onto ice (500 g)
  4. extractionThe mixture was extracted twice with 700 mL of ethyl acetate
  5. customThe organic solvent was removed

Sources & evidence

ORD record
ord-9d855beeada3426f87519cf2d1817424
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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