N-Methylmaleimide → HCID 21543112, compound

HRID 1606497Notes

Reaction equation

HRID 1606497 reaction equation
[CH3:1][N:2]1[CH2:7][C:6]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH2:4][CH2:3]1.[CH3:18][N:19]1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1=[O:25]>C1(C=CC(O)=CC=1)O.C1(C)C=CC=CC=1>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH:9]2[CH:8]=[C:6]3[CH:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH2:7]3)[CH:21]3[C:20](=[O:25])[N:19]([CH3:18])[C:23](=[O:24])[CH:22]23)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 70261N-MethylmaleimideHCID 54082386HCID 54082386, compound

Product 1

HCID 21543112HCID 21543112, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 1140TolueneSolvent

Procedure

A solution of 15 g (0.065 moles) 1,2,3,6-tetrahydro-1-methyl-5-p-methoxystyrylpyridine (free base), 15 g N-methylmaleimide, 150 ml toluene and 20 mgs hydroquinone is refluxed under nitrogen overnight. The solution is allowed to cool and evaporate. Benzene is added and evaporated twice. Water is added, and the oil is extracted with benzene. The organic layers are evaporated. The residue crystallizes and filtration and washing with ether yields 7.85 g 3a,4,6,7,8,9,9a,9b-octahydro-4-(p-methoxyphenyl)-2,7-dimethyl-2H-pyrrolo[3,4-f]-isoquinoline-1,3-dione. Chromatography of the mother liquor on basic alumina (activity II) yields an additional 3.2 g (50%) cyrstals.

Workup

  1. temperatureto cool
  2. customevaporate
  3. additionBenzene is added
  4. customevaporated twice
  5. additionWater is added
  6. extractionthe oil is extracted with benzene
  7. customThe organic layers are evaporated
  8. customThe residue crystallizes
  9. filtrationfiltration
  10. washwashing with ether

Sources & evidence

ORD record
ord-a0c52ea425384c71bf908b1fa914dd98
Source dataset
uspto-grants-1976_04
Patent number
US03953434

Reaction notes

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