Benzene → 3-Benzoylpyridine-2-carboxylic acid

HRID 1721599Notes

Reaction equation

HRID 1721599 reaction equation
[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([O:5][C:6]2=[O:11])=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:6]([C:7]1[C:2]([C:3]([OH:5])=[O:4])=[N:1][CH:10]=[CH:9][CH:8]=1)(=[O:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 7269413-Benzoylpyridine-2-carboxylic acid

Procedure

10 g (67 mmol) quinolinic acid anhydride was suspended in 50 ml benzene and 17.9 g (134 mmol) AlCl3 was added in portions while cooling on ice. After completion of the addition, it was stirred for a further 3 hours at room temperature, carefully admixed with ice and aspirated from the precipitate which was present. The crude product was purified by column chromatography on silica gel 60 using ethyl acetate/dichloromethane 1/1 as the eluent.

Workup

  1. temperaturewhile cooling on ice
  2. additionAfter completion of the addition, it
  3. customThe crude product was purified by column chromatography on silica gel 60 using ethyl acetate/dichloromethane 1/1 as the eluent

Sources & evidence

ORD record
ord-cb8b0a94163740858d6ea364cff5334b
Source dataset
uspto-grants-1996_04
Patent number
US05512564

Reaction notes

Loading…