Methylamine → (2Z)-4-(Methylamino)-4-oxo-2-butenoic acid

HRID 868688Notes

Reaction equation

HRID 868688 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH3:8][NH2:9]>ClC1C=CC=CC=1>[CH3:8][NH:9][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 7923Maleic Anhydride

Product 1

HCID 5354909(2Z)-4-(Methylamino)-4-oxo-2-butenoic acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

The same reactor as used in Example 7 was adopted. This reactor was charged with a solution 53 g of maleic anhydride in 200 g of chlorobenzene. Then, methylamine gas was blown in gradually and piecemeal at 30° C. at a rate of 4.3×10-3 mol/min. over a period of two hours to produce a white slurry of N-methyl maleinamic acid. Subsequently, the slurry and 22.5 g of ortho-phosphoric acid (purity 89% by weight), 0.1 g of phenothiazine, and 0.02 g of zinc acetate added thereto were heated at 134° C. for two hours to effect reaction. Thereafter, the resultant reaction mixture was cooled to 40° C., filtered, and distilled under a vacuum to expel chlorobenzene. Consequently, there was obtained 45 g of light yellow N-methyl maleimide having purity of 92.1% by weight. The yield of the product is calculated to be 72.5 mol % based on methylamine as the raw material.

Workup

  1. custompiecemeal at 30° C.
  2. customof two hours

Sources & evidence

ORD record
ord-f668431f79e5476597e756ec622aff66
Source dataset
uspto-grants-1988_10
Patent number
US04780546

Reaction notes

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