4-Aminophenol → 2-(4-Hydroxyphenylamino)-2-methylpropanenitrile

HRID 2233665

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[O-]S([O-])(=O)=O.[Mg+2].[CH3:15][C:16]([CH3:20])(O)[C:17]#[N:18]>>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16]([CH3:20])([CH3:15])[C:17]#[N:18])=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 4034-Aminophenol

HCID 6406Acetone Cyanohydrin

HCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 3502692-(4-Hydroxyphenylamino)-2-methylpropanenitrileYield 96%

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-aminophenol (1.09 g, 10 mmol), acetone cyanohydrin (10 ml) and MgSO4 (2 g) was heated to 80° C. and stirred for 4 h. After concentration of the medium under vacuum, compound 3a was crystallized from water (20 ml). The solid was filtered and dried to yield 2-(4-hydroxyphenylamino)-2-methylpropanenitrile, 3a (1.69 g, 9.6 mmol, 96%).

Workup

customAfter concentration of the medium under vacuum, compound 3a was crystallized from water (20 ml)
filtrationThe solid was filtered
customdried

Sources & evidence

ORD record: ord-0cb27252f9b747538627e043f3f082ed
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709517B2

Linked notes

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