Phthalic Anhydride → N-Methylphthalimide

HRID 1855930Notes

Reaction equation

HRID 1855930 reaction equation
O([C:8]1[CH:9]=[C:10]2[C:15](=[O:16])[N:14]([CH3:17])[C:12](=[O:13])[C:11]2=[CH:18][CH:19]=1)C1C=CC=CC=1.C1(=O)OC(=O)C2=CC=CC=C12>>[CH3:17][N:14]1[C:12](=[O:13])[C:11]2=[CH:18][CH:19]=[CH:8][CH:9]=[C:10]2[C:15]1=[O:16]

Participants

3

Reactant 2

HCID 6811Phthalic AnhydrideHCID 8215562-methyl-5-phenoxyisoindole-1,3-dione

Product 1

HCID 11074N-MethylphthalimideYield 46%

Procedure

The above results show that an exchange occurred between 4-phenoxy-N-methylphthalimide and phthalic anhydride, resulting in a 46% yield of N-methylphthalimide and a 64% yield of 4-phenoxyphthalic anhydride or acid. This conversion of 4-phenoxy-N-methylphthalimide to 4-phenoxyphthalic anhydride was achieved in a direct manner without any requirement for converting the 4-phenoxy-N-methylphthalimide to the corresponding hydrazide or the base hydrolysis thereof, resulting in the production of metal salt requiring the neutralization and heating of the resulting phthalic acid.

Workup

  1. customThe above results

Sources & evidence

ORD record
ord-796184338a7c4165a53017e35c02ff7c
Source dataset
uspto-grants-1980_08
Patent number
US04217281

Reaction notes

Loading…