1H,3H-furo(3,4-c)pyridine-1,3-dione → N-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-3,4-dicarboximide

HRID 352532

Reaction equation

HRID 352532 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]2[C:7]([O:9][C:10](=[O:11])[C:3]=2[CH:2]=1)=O.[F:12][C:13]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24]([CH3:29])[CH:23]=1)([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15]>C1COCC1>[F:12][C:13]([C:22]1[CH:28]=[CH:27][C:25]([N:26]2[C:7](=[O:9])[C:4]3[CH:5]=[CH:6][N:1]=[CH:2][C:3]=3[C:10]2=[O:11])=[C:24]([CH3:29])[CH:23]=1)([C:18]([F:19])([F:20])[F:21])[C:14]([F:17])([F:16])[F:15]

Participants

4

Reactant 2

HCID 2783981H,3H-furo(3,4-c)pyridine-1,3-dioneHCID 99255434-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2-methylaniline

Product 1

HCID 22712038N-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-3,4-dicarboximide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of THF were dissolved 1.50 g of pyridine-3,4-dicarboxylic acid anhydride and 2.75 g of 4-(heptafluoro-2-propyl)-2-methylaniline, and the reaction was carried out at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and 20 ml of trifluoroacetic anhydride was added to the resulting residue, and the reaction was carried out with refluxing for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain crude N-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-3,4-dicarboximide quantitatively.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure and 20 ml of trifluoroacetic anhydride
  3. additionwas added to the resulting residue
  4. temperaturewith refluxing for 3 hours
  5. customAfter completion of the reaction
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-202579acd3bf46baa0df4b8eb4c95e2c
Source dataset
uspto-grants-2004_06
Patent number
US06747041B1

Linked notes

Loading…