N-methyl-4-chlorophthalimide → 2-methyl-5-phenoxyisoindole-1,3-dione

HRID 2417900Notes

Reaction equation

[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Cl[C:10]1[CH:11]=[C:12]2[C:17](=[O:18])[N:16]([CH3:19])[C:14](=[O:15])[C:13]2=[CH:20][CH:21]=1>>[O:1]([C:10]1[CH:11]=[C:12]2[C:17](=[O:18])[N:16]([CH3:19])[C:14](=[O:15])[C:13]2=[CH:20][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 246078N-methyl-4-chlorophthalimide

HCID 4445035Phenolate Sodium

Product 1

HCID 8215562-methyl-5-phenoxyisoindole-1,3-dioneYield 45.6%

Conditions

Temperature: 250 °C

Procedure

A mixture of 0.440 g (3.80 mmol) of anhydrous sodium phenoxide and 1.50 g (76.7 mmol) of 4-chloro-N-methyl phthalimide is heated to 250° C. for 4 hours under a nitrogen gas atmosphere in an autoclave. There was obtained a 45.6% yield of 4-phenoxy-N-methyl phthalimide based on the phenoxide as determined by gas or liquid chromatographic analysis using o-terphenyl as an internal standard. The product was identified by a comparison of its retention time with that of an authentic sample of the desired material in a conventional matter.

Sources & evidence

ORD record: ord-d1adda8ac9844fb7aaba02976914dc8c
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04471125

Reaction notes

Loading…