2-Methoxy-4-nitroaniline → HCID 21834796, compound

HRID 1741184Notes

Reaction equation

HRID 1741184 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1N.C(ON=O)(C)(C)C.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Cu]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:4]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:3]=2[O:2][CH3:1])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 73372-Methoxy-4-nitroanilineHCID 7964ChlorobenzeneHCID 10906Tert-Butyl nitrite

Product 1

HCID 21834796HCID 21834796, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

2-Methoxy4-nitroaniline 5 and chlorobenzene are heated in the presence of t-butylnitrite and copper powder to give 2-(4-chlorophenyl)-5-nitroanisole 6. Hydrogenation of 6 with platinum oxide in methanol (a base such as morpholine may be used) provides the desired biphenyl amine 3.

Sources & evidence

ORD record
ord-1fec073ffe734c35b92868f1b597a6d3
Source dataset
uspto-grants-1999_10
Patent number
US05973008

Reaction notes

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