Nitrogen oxide (N2O4) → 3-(4-Carboxyphenyl)-2-nitronaphtho-[1,2-b]furan

HRID 443357

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:12]=3[O:13][CH:14]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[N+:23]([O-:28])([N+]([O-])=O)=[O:24]>C(Cl)(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:12]=3[O:13][C:14]=2[N+:23]([O-:28])=[O:24])=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of 4.0 g. of the product of step A in 250 ml. of chloroform is added 4.0 g. of dinitrogen tetraoxide. The mixture is stirred at about 20° C. for 20 hours. The mixture is filtered, and the solid obtained is recrystallized from a mixture of N,N-dimethylformamide and water to provide yellow crystals of 3-(4-carboxyphenyl)-2-nitronaphtho-[1,2-b]furan, m.p. greater than 300° C.

Workup

additionTo a mixture of 4.0 g
filtrationThe mixture is filtered
customthe solid obtained
customis recrystallized from a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record: ord-e28d80b5dfe34e09bc94167fff3c1a07
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04260547

Linked notes

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