Aniline → 4-Nitroaniline

HRID 329152Notes

Reaction equation

HRID 329152 reaction equation
[N+:1]([O-:6])([N+:3]([O-:5])=[O:4])=[O:2].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1C=CC=CC=1>[NH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[N:1]=[N:3][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+:1]([O-:6])([N+:3]([O-:5])=[O:4])=[O:2].[N+:1]([C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][CH:10]=1)([O-:6])=[O:2]

Participants

6

Reactant 2

HCID 6115AnilineHCID 25352Nitrogen oxide (N2O4)

Product 3

HCID 74754-NitroanilineHCID 8689DiazoaminobenzeneHCID 25352Nitrogen oxide (N2O4)

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Primary aromatic amines also have been diazotized in solvents by means of pure nitrogen tetroxide. O. N. Witt, Tagbl. Natf.-Vers. Baden-Baden 1879, 194 (Chem. Zentr. 1880, II, 226) reported obtaining benzenediazonium nitrate by the reaction of anhydrous pure nitrogen tetroxide with aniline in an anhydrous benzene solution; and B. Houston et al., J. Am. Chem. Soc. 47, 3011-3018 (1925), obtained a diazoaminobenzene derivative as well as the corresponding diazonium nitrate by the action of pure, anhydrous nitrogen tetroxide on o-, m-, and p-nitroaniline in an anhydrous benzene solution.

Sources & evidence

ORD record
ord-368793d34a104beeb6b437a34378f80c
Source dataset
uspto-grants-1977_04
Patent number
US04020052

Reaction notes

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