2-Aminophenol → 3-chloro-N-(2-hydroxyphenyl)propanamide

HRID 456400Notes

Reaction equation

HRID 456400 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Cl:9][CH2:10][CH2:11][C:12](Cl)=[O:13]>CC(C)=O.O>[Cl:9][CH2:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:13]

Participants

5

Reactant 2

HCID 58012-AminophenolHCID 693643-Chloropropionyl chloride

Product 1

HCID 34055143-chloro-N-(2-hydroxyphenyl)propanamideYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of 2-aminophenol (2.18 g, 20 mmol) in acetone (20 mL) a solution of 3-chloropropionyl chloride (1.28 g, 0.87 mL, 10 mmol) in acetone (20 mL) was added dropwise. After the addition was completed, the reaction mixture was stirred at room temperature for 0.5 h and then diluted with water (50 mL). Acetone was removed in vacuo, the precipitate formed was collected by filtration, washed with water, and dried to give the subtitle compound (1.53 g, 77%).

Workup

  1. additionAfter the addition
  2. customAcetone was removed in vacuo
  3. customthe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-031321934757477598d9f1ae112bd41c
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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