Pyridine → Phthalic Anhydride

HRID 971455Notes

Reaction equation

HRID 971455 reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6](=[O:11])[C:7](F)(F)F)=[O:4].N1C=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[C:3]1(=[O:4])[O:5][C:6](=[O:11])[C:7]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]12

Participants

4

Reactant 2

HCID 1049PyridineHCID 9845Trifluoroacetic anhydride

Product 1

HCID 6811Phthalic Anhydride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

22.4 g (0.08 mol) of the 4-(maleinamidyl)-phthalic acid manufactured according to Example 3, paragraph 1, are suspended in 150 ml of anhydrous methylene chloride and 37.8 ml of trifluoroacetic anhydride are added. The reaction mixture is stirred for 2 hours at 20°-25° C., whilst excluding atmospheric moisture. 30.5 g of pyridine are then added dropwise whilst cooling with ice (internal temperature 20°-25° C.). The reaction mixture is then stirred for a further 2 hours at 20°-25° C. and filtered, and the filter residue is washed with a little methylene chloride and dried under a high vacuum. 14.7 g (75% of theory) of 4-isomaleinimidyl)-phthalic anhydride are obtained in the form of slightly yellowish crystals; decomposition at 195°-207° C.

Workup

  1. temperaturewhilst cooling with ice (internal temperature 20°-25° C.)
  2. stirringThe reaction mixture is then stirred for a further 2 hours at 20°-25° C.
  3. filtrationfiltered
  4. washthe filter residue is washed with a little methylene chloride
  5. customdried under a high vacuum

Sources & evidence

ORD record
ord-fc4f94bc326541c784d07a7b030493b4
Source dataset
uspto-grants-1979_07
Patent number
US04160081

Reaction notes

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