Phthalimide → bicyclo[4.2.0]octa-1,3,5-trien-7-amine

Reaction equation

[C:1]1(=O)[NH:5][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(=O)NC(=O)C=C1.C1(C2C(=CC=CC=2)CO1)=O>>[NH2:5][CH:1]1[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[CH2:4]1

Participants

Reactant 3

HCID 6809Phthalimide

HCID 6885Phthalide

HCID 10935Maleimide2×

Product 1

HCID 2753029bicyclo[4.2.0]octa-1,3,5-trien-7-amine

Procedure

An alternative process is that wherein a 3- or 4-halobenzocyclobutene reactant is treated with a phthalimide or maleimide to produce a 3- or 4-phthalimido-or maleimidobenzocyclobutene. When phthalimide or maleimide is monomeric, for example, phthalide or maleimide themselves, the product can be cleaved by reaction with an amine to produce a corresponding aminobenzocyclobutene. A preferred amine for this purpose is hydrazine, preferably hydrazine hydrate.

Sources & evidence

ORD record: ord-a1b9506f39aa42abbdfb9e3b6d6959fb
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05274135

Reaction notes

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