Pyridine → 2-Phenylfuro[3,4-b]pyridine-5,7-dione

HRID 1462594Notes

Reaction equation

HRID 1462594 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]([OH:15])=O)[C:10]([C:16]([OH:18])=[O:17])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(=O)C)(=O)C.N1C=CC=CC=1>C(COC)OC>[C:1]1([C:7]2[N:12]=[C:11]3[C:13]([O:18][C:16](=[O:17])[C:10]3=[CH:9][CH:8]=2)=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13345315HCID 13345315, compound

Product 1

HCID 133453222-Phenylfuro[3,4-b]pyridine-5,7-dioneYield 91.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5.56 g (22.9 mmol) of 6-phenyl-2,3-pyridinedicarboxylic acid and 7 ml (121.8 mmol) of acetic anhydride in 25 ml of dimethoxyethane (DME) is added 3.7 ml (45.7 mmol) of pyridine. A small exotherm ensues, and the anhydride begins to precipitate. After one hour, the reaction mixture is diluted with ether and hexane to the cloud point, chilled in an ice bath, and filtered. The solid is washed with ether to give 4.73 g of the desired anhydride as a white solid, mp 187°-192° C.

Workup

  1. customto precipitate
  2. additionthe reaction mixture is diluted with ether and hexane to the cloud point
  3. temperaturechilled in an ice bath
  4. filtrationfiltered
  5. washThe solid is washed with ether

Sources & evidence

ORD record
ord-87aeb5f0c9464234ad93f6674f5a4290
Source dataset
uspto-grants-1984_07
Patent number
US04460776

Reaction notes

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