Methylamine → N-Methylphthalimide

HRID 1859263Notes

Reaction equation

HRID 1859263 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][NH2:13]>O>[CH3:12][N:13]1[C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]2[C:1]1=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 6811Phthalic Anhydride

Product 1

HCID 11074N-Methylphthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 25.0 g (0.17 mol) of phthalic anhydride in 200 ml of water was added 30 g (0.38 mol) of a 40% aqueous solution of methylamine. The mixture was heated at reflux for four hours, after which approximately 50 ml of the aqueous amine was removed by distillation and the mixture allowed to cool. The resultant precipitate was collected by filtration to yield 10.3 g of N-methylphthalimide (cyclic imide (b)(4)).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for four hours
  3. customafter which approximately 50 ml of the aqueous amine was removed by distillation
  4. temperatureto cool
  5. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-f3ea0461205e4806af5cda5dd2b6f280
Source dataset
uspto-grants-2000_11
Patent number
US06153764

Reaction notes

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