N-Hydroxyphthalimide → Phthalaldehyde

HRID 1532479Notes

Reaction equation

HRID 1532479 reaction equation
[N]=O.ON1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14]>C(#N)C>[CH:5](=[O:14])[C:6]1[C:7](=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 145068Nitric Oxide

Product 1

HCID 4807PhthalaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A total of 13 mmol of nitrogen monoxide was introduced into a mixture of 1 mmol of 1-hydroxyphthalan, 0.1 mmol of N-hydroxyphthalimide, and 5 ml of acetonitrile, and the resultant mixture was stirred at 60° C. for 2 hours. Isolation of products in the reaction mixture by column chromatography on a silica gel revealed that 1-hydroxyphthalane was converted, at a rate of 99%, into phthalaldehyde (yield: 95%).

Sources & evidence

ORD record
ord-5d78b535f7cb4729b1d93dd2da46708d
Source dataset
uspto-grants-2001_03
Patent number
US06201156B1

Reaction notes

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