4-Amino-4'-hydroxybiphenyl → 2-Chloro-4-nitro-4'-(4-hydroxyphenyl)azobenzene

HRID 65175Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[N:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 0.840 g of 2-chloro-4-nitro-1-nitrosobenzene in 20 ml of glacial acetic acid was heated to 70° C. and treated while stirring with a solution, heated to 110° C., of 0.926 g of 4-amino-4'-hydroxybiphenyl [prepared according to Chem. Berichte 27 (1894) 2627] in 43 ml of glacial acetic acid. The dark solution was stirred at 70° C. for a further 2.25 hours, then cooled to room temperature and extracted with methylene chloride. The extracts were washed with water, 10% sodium hydrogen carbonate solution and again with water, dried over sodium sulphate and concentrated in vacuo. Thus yielding 1.3 g of crude 2-chloro-4-nitro-4'-(4-hydroxyphenyl)azobenzene as brown crystals.

Workup

additiontreated
stirringThe dark solution was stirred at 70° C. for a further 2.25 hours
temperaturecooled to room temperature
extractionextracted with methylene chloride
washThe extracts were washed with water, 10% sodium hydrogen carbonate solution and again with water
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-eee20e3f3d714805a25e7ed6eb4a5784
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04613208

Reaction notes

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