Maleic Anhydride → HCID 21527739, compound

HRID 1658519Notes

Reaction equation

HRID 1658519 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[ClH:8].[CH3:9][N:10]1[CH2:15][CH:14]=[C:13]([CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][CH2:11]1>C(O)(=O)C>[ClH:8].[CH3:9][N:10]1[CH2:11][CH2:12][C:13]2[CH:14]([CH:3]3[C:4](=[O:5])[O:6][C:1](=[O:7])[CH:2]3[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 68131268HCID 68131268, compound

Product 1

HCID 21527739HCID 21527739, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 50 g. maleic anhydride and 10 g. 1,2,3,6-tetrahydro-1-methyl-4-styrylpyridine hydrochloride, from example 7, in 100 ml. acetic acid and 100 ml. acetic anhydride previously thoroughly sparged with dry nitrogen is refluxed gently for 3 hours under nitrogen. The reaction mixture is concentrated to 100 ml. volume, and flushed with 300 ml. benzene to remove most of the remaining solvent. The residue is triturated with benzene several times to give 17.5 g. of a crude brown product. This compound is not further purified. It is refrigerated in the dry state for storage.

Workup

  1. customacetic anhydride previously thoroughly sparged with dry nitrogen
  2. temperatureis refluxed gently for 3 hours under nitrogen
  3. concentrationThe reaction mixture is concentrated to 100 ml
  4. customvolume, and flushed with 300 ml
  5. custombenzene to remove most of the remaining solvent
  6. customThe residue is triturated with benzene several times
  7. customto give 17.5 g

Sources & evidence

ORD record
ord-c3430675865e445c821d4692770c318c
Source dataset
uspto-grants-1976_06
Patent number
US03965102

Reaction notes

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