4-Aminophenol → HCID 67285924, compound

HRID 244987Notes

Reaction equation

HRID 244987 reaction equation
C[Si]([C:5]#[N:6])(C)C.[OH:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1.[C:15]1(=O)[CH2:18][CH2:17][CH2:16]1.ClCCl>CC(C)=O>[OH:7][C:8]1[CH:14]=[CH:13][C:11]([NH:12][C:15]2([C:5]#[N:6])[CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 6344DichloromethaneHCID 14496CyclobutanoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 67285924HCID 67285924, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Trimethylsilyl cyanide (0.93 ml, 7 mmol) was added dropwise to a mixture of 4-hydroxyaniline (0.545 g, 5 mmol) and cyclobutanone (0.42 g, 6 mmol). The reaction mixture was stirred at room temperature for 6 h and then concentrated under vacuum to obtain a brown liquid which was subjected to chromatography (dichloromethane:acetone, 98:2) to yield 11a (0.903 g, 4.8 mmol, 96%) as a yellowish solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customto obtain a brown liquid which

Sources & evidence

ORD record
ord-0c186e5c3cb94d9aa83f11558dd0deab
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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