Methylamine → N-methyl-4-chlorophthalimide

Reaction equation

[Cl:1][CH:2]1[CH:12]=[CH:11][CH:5]2[C:6]([O:8][C:9](=O)[CH:4]2[CH2:3]1)=[O:7].[CH3:13][NH2:14]>>[CH3:13][N:14]1[C:9](=[O:8])[C:4]2=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=[C:5]2[C:6]1=[O:7]

Participants

Reactant 2

HCID 6329Methylamine

HCID 54187688HCID 54187688, compound

Product 1

HCID 246078N-methyl-4-chlorophthalimideYield 95%

Conditions

Temperature: 150 °C

Procedure

An appropriately equipped glass reaction vessel was charged with 186.5 grams (1 mole) of 4-chlorotetrahydrophthalic anhydride and heated to 150° C. under nitrogen. Methylamine gas (32 grams, 1.03 mole) was then introduced to the reaction vessel subsurface over 30 minutes. The reaction mixture was then heated for 3 hours at 180° C. The product was then distilled to give N-methyl-4-chlorophthalimide in approximately 95% yield.

Workup

customAn appropriately equipped glass reaction vessel
temperatureThe reaction mixture was then heated for 3 hours at 180° C
distillationThe product was then distilled

Sources & evidence

ORD record: ord-18a8d1327da74491bcd01ca1326c2c4b
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528663B1

Reaction notes

Loading…