Aniline → 4-Nitrosoaniline

HRID 1267718Notes

Reaction equation

HRID 1267718 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-:10])=[O:9].[Na+]>>[N:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)=[O:10].[N:8]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9]

Participants

4

Reactant 2

HCID 6115AnilineHCID 23668193Sodium Nitrite

Product 2

HCID 695744-NitrosoanilineHCID 181501Nitrous amide, N-phenyl-

Procedure

Conventionally, 4-nitrosoaniline is prepared by contacting aniline with sodium nitrite (NaNO2) to produce N-nitrosoaniline and then subjecting the N-nitrosoaniline to Fischer-Hepp rearrangement in acidic condition (Tetrahedron, 1975, 31, 1343-9), or by contacting p-nitrosophenol with ammonia or ammonium chloride (NH4Cl) (U.S. Pat. No. 3,338,966; and J. Chem. Soc., 1955, 2049).

Sources & evidence

ORD record
ord-d6d76e942fdc445ba8a0dff14821f018
Source dataset
uspto-grants-2003_04
Patent number
US06552229B1

Reaction notes

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