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

HRID 515800Notes

Reaction equation

HRID 515800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].O[C:16]([CH3:20])([CH3:19])[C:17]#[N:18]>>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16]([CH3:20])([CH3:19])[C:17]#[N:18])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 4034-AminophenolHCID 6406Acetone CyanohydrinHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 3502692-(4-Hydroxyphenylamino)-2-methylpropanenitrileYield 74%

Conditions

Temperature
80 °C

Procedure

A mixture of 4-aminophenol (1 g, 9.17 mmol) and magnesium sulfate (4 g) in 2-hydroxy-2-methylpropanenitrile (10 mL) was heated to 80° C. for 2 h. Ice/water was added to a cooled mixture and it was stirred for 30 min. The white solid that precipitated was filtered, washed with water, and dried to afford 1.2 g (74%) of 2-((4-hydroxyphenyl)amino)-2-methylpropanenitrile as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 6.78 (d, 2H), 6.65 (d, 2H), 5.21 (s, 1H), 1.52 (s, 6H).

Workup

  1. customThe white solid that precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a1bdbc89d1d047ab99906ff1924f997d
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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