Nitric Acid → Benzonitrile, 4-chloro-3-nitro-

HRID 2292264Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11]>>[N+:10]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[Cl:1])[C:6]#[N:7])([O-:12])=[O:11]

Participants

Reactant 2

HCID 944Nitric Acid

HCID 121634-Chlorobenzonitrile

Product 1

HCID 13655Benzonitrile, 4-chloro-3-nitro-

Procedure

4-chloro-benzonitrile was reacted with nitric acid to obtain 3-nitro-4-chloro-benzonitrile melting at 100°-101° C. which was reacted with N-hydroxy-phthalimide to obtain 0-(4-cyano-2-nitrophenoxy)-phthalimide melting at 233°-234° C. The latter was reacted to obtain 0-(4-cyano-2-nitro-phenyl)-hydroxylamine melting at 154°-155° C.

Sources & evidence

ORD record: ord-201a863b588547149858d057194c5b16
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801717

Reaction notes

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