Acetic Anhydride → HCID 54286994, compound

HRID 2372184Notes

Reaction equation

HRID 2372184 reaction equation
C([O-])(=O)C.[Na+].[C:6]([O:9][C:10](=[O:12])[CH3:11])(=[O:8])[CH3:7].[CH3:13][N:14]([CH3:21])[N:15]=[CH:16][C:17]([CH2:19][CH3:20])=[CH2:18].BrC1C(OC(=O)C=1)=O>C(Cl)Cl>[CH3:13][N:14]([CH3:21])[N:15]1[CH:16]=[C:17]([CH2:19][CH3:20])[CH2:18][C:7]2[C:6]([O:9][C:10](=[O:12])[C:11]1=2)=[O:8]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 800273-Bromo-2,5-furandioneHCID 517045Sodium AcetateHCID 53941239HCID 53941239, compound

Product 1

HCID 54286994HCID 54286994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of sodium acetate (14.76 g, 180.0 mmol) and acetic anhydride (150 ml) is heated, under N2, to 120° for 10 min., and is then chilled to 10°. 2-Ethyl-2-propenal dimethylhydrazone (11.36 g, 90.0 mmol) is added, followed by addition of bromomaleic anhydride (16.41 g, 92.7 mmol) and the reaction mixture is stirred at 10° for ca. 1 hour. The mixture is then diluted with methylene chloride and filtered, and the solid is rinsed with methylene chloride until colorless. The filtrate is concentrated to remove the solvent and to give 1,4-dihydro-1-dimethylamino-5-ethyl-2,3-pyridinedicarboxylic anhydride.

Workup

  1. temperatureis heated, under N2, to 120° for 10 min.
  2. temperatureis then chilled to 10°
  3. filtrationfiltered
  4. washthe solid is rinsed with methylene chloride until colorless
  5. concentrationThe filtrate is concentrated
  6. customto remove the solvent

Sources & evidence

ORD record
ord-13b5d89e4a7a4b2da5609da5220a5398
Source dataset
uspto-grants-1992_03
Patent number
US05098462

Reaction notes

Loading…