Phosphorus oxychloride → 4-Chloro-furo[3,4-c]quinoline-1,3-dione

HRID 5129Notes

Reaction equation

HRID 5129 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:15]([OH:17])=[O:16])=[C:8]([C:12]([OH:14])=O)[C:9]([NH:11][C:4]2=[CH:3][CH:2]=1)=O.P(Cl)(Cl)([Cl:20])=O>CN(C)C=O>[Cl:20][C:9]1[C:8]2[C:12](=[O:14])[O:17][C:15](=[O:16])[C:7]=2[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 8045962-Oxo-1,2-dihydroquinoline-3,4-dicarboxylic acid

Product 1

HCID 541042384-Chloro-furo[3,4-c]quinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 2(1H)-Oxo-quinoline-3,4-dicarboxylic acid (2.0 g), phosphorous oxychloride (10 mL) and 8 drops of dimethyl formamide was refluxed with stirring for 20 min. The reaction mixture was concentrated in vacuo and the residue treated with ice water to afford 4-Chloro-furo[3,4-c]quinoline-1,3-dione as a tan solid.

Workup

  1. temperaturewas refluxed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue treated with ice water

Sources & evidence

ORD record
ord-72ad1c3127de403cb4e6f9720380d252
Source dataset
uspto-grants-1993_09
Patent number
US05243049

Reaction notes

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