4-Aminophenol → 2-chloro-N-(4-hydroxyphenyl)acetamide

HRID 1053586Notes

Reaction equation

HRID 1053586 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][CH2:10][C:11](Cl)=[O:12]>CC(O)=O.CC(O[Na])=O>[Cl:9][CH2:10][C:11]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)=[O:12]

Participants

5

Reactant 2

HCID 4034-AminophenolHCID 6577Chloroacetyl chloride

Product 1

HCID 2363232-chloro-N-(4-hydroxyphenyl)acetamideYield 40.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 178418247HCID 178418247, compoundSolvent

Procedure

To a solution of 4-aminophenol (1.0 g, 9.1 mmol) in CH3COOH (3.5 mL) and saturated CH3COONa (3.5 mL), chloroacetylchloride (0.72 mL, 9.1 mmol) was added dropwise. After the addition was complete, the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated, washed with water (3×25 mL) and dried over vacuum to isolate the intermediate 17a as white solid (0.690 g, 3.71 mmol, 40% yield). 1H NMR (DMSO, 400 MHz) δ 10.03 (s, 1H), 9.27 (s, 1H), 7.36 (d, J=8.8 Hz, 2H), 6.71 (d, J=8.8 Hz, 2H) 4.182 (s, 2H).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated
  3. washwashed with water (3×25 mL)
  4. customdried over vacuum

Sources & evidence

ORD record
ord-a99683c01c874142b812d9901835f1c0
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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