Acetic Anhydride → 5,9-Bis(2,2,2-trifluoroethoxy)furo[3,4-g]quinoline-6,8-dione

HRID 907470Notes

Reaction equation

HRID 907470 reaction equation
[F:1][C:2]([F:28])([F:27])[CH2:3][O:4][C:5]1C(C(O)=O)=C(C(O)=O)[C:12]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2.[C:29]([O:32][C:33](=[O:35])[CH3:34])(=[O:31])[CH3:30]>>[F:28][C:2]([F:1])([F:27])[CH2:3][O:4][C:5]1[C:30]2[C:29](=[O:31])[O:32][C:33](=[O:35])[C:34]=2[C:12]([O:21][CH2:22][C:23]([F:25])([F:26])[F:24])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 442453435,8-Bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylic acid

Product 1

HCID 442455085,9-Bis(2,2,2-trifluoroethoxy)furo[3,4-g]quinoline-6,8-dioneYield 96%

Procedure

A solution of 5,8-bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylic acid 4 (180 mmol) in acetic anhydride (500 ml) was heated to reflux for 3 h and concentrated to dryness. The solid residue was triturated into 400 ml ether:hexane 1:4 to afford 68.2 g (96% yield for the last two steps) of the anhydride as a brownish solid.

Workup

  1. temperatureto reflux for 3 h
  2. concentrationconcentrated to dryness
  3. customThe solid residue was triturated into 400 ml ether:hexane 1:4

Sources & evidence

ORD record
ord-fe3babd31d6f4c3baf0e4248065bcbd6
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

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