2-Aminophenol → 2-chloro-N-(2-hydroxyphenyl)acetamide

HRID 132979Notes

Reaction equation

HRID 132979 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)(O)[O-].[Na+].C(#N)C.[Cl:17][CH2:18][C:19](Cl)=[O:20]>CO.O>[Cl:17][CH2:18][C:19]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:20]

Participants

7

Reactant 4

HCID 58012-AminophenolHCID 6342AcetonitrileHCID 6577Chloroacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 3505672-chloro-N-(2-hydroxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

109.1 g (1 mol) of 2-aminophenol, 84.1 g (1 mol) of sodium bicarbonate, 900 mL of acetonitrile and 100 mL of water were added under room temperature into a 2 L flask with four inlets and attached with a stirrer and a thermometer. The internal temperature was cool down to 10° C. and 112.9 g (1 mol) of chloroacetyl chloride was added to the solution over a period of 3 hours and stirred for 3 hours at room temperature. Following to the completion of the reaction, 10 mL of methanol was added, and then acetonitrile was distilled out under reduced pressure and the resultant residue was subjected to recrystallization with toluene. Then, salt was taken out in a cleaning process using water to obtain 2-chloroacetyl-2-hydroxyaniline.

Workup

  1. customattached with a stirrer
  2. additionwas added
  3. distillationacetonitrile was distilled out under reduced pressure
  4. customthe resultant residue was subjected to recrystallization with toluene

Sources & evidence

ORD record
ord-77dc95c0317e4e03a3db2747c77a5cd5
Source dataset
uspto-grants-2008_06
Patent number
US07390771B2

Reaction notes

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