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

HRID 2291793Notes

Reaction equation

HRID 2291793 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-phenylpyridine-2,3-dicarboxylic 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-09b732666d5a41f9aea5066c0259af1b
Source dataset
uspto-grants-1989_01
Patent number
US04798619

Reaction notes

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