4-Amino-4'-nitrobiphenyl → 4-Amino-4'-(p-nitrophenyl)azobenzene

HRID 1075131Notes

Reaction equation

HRID 1075131 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([N:26]=O)=[CH:22][CH:21]=1)([O-])=O.S.[Na]>C(O)C>[NH2:17][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[N:16][C:13]2[CH:14]=[CH:15][C:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)=[CH:11][CH:12]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 145934-Amino-4'-nitrobiphenylHCID 6435471-Nitro-4-nitrosobenzeneHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 204941674-Amino-4'-(p-nitrophenyl)azobenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The preparation of a compound of formula XII in which m is the integer 2 and X is alkoxy and Y is p-nitrophenyl can be carried out, for example, by reacting 4-nitro-4'-aminobiphenyl with 4-nitro-nitrosobenzene, partially reducing the resulting compound with sodium hydrogen sulfide in ethanol according to Houben-Weyl XI/1, 418, to give 4-amino-4'-(p-nitrophenyl)azobenzene, diazotizing this with sodium nitrite and hydrochloric acid, coupling the diazonium salt with phenol and etherifying the resulting compound with a 1-bromoalkane in ethanol in the presence of potassium carbonate and sodium iodide.

Sources & evidence

ORD record
ord-3e0a07d58eca4fb28464995f3de68f35
Source dataset
uspto-grants-1983_07
Patent number
US04395350

Reaction notes

Loading…