Nitric Acid → N-(5-Chloro-2-hydroxy-3-nitrophenyl)acetamide

HRID 1824707Notes

Reaction equation

HRID 1824707 reaction equation
[NH:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[OH:12])[C:2]([CH3:4])=[O:3].[N+:13]([O-])([OH:15])=[O:14].O>C(OC(=O)C)(=O)C>[NH:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[C:6]=1[OH:12])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 952582-Acetylamino-4-chlorophenol

Product 1

HCID 22142329N-(5-Chloro-2-hydroxy-3-nitrophenyl)acetamideYield 31%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Under ice cooling, a solution of 2-acetamino-4-chlorophenol (1.0 g, 5.4 mmol) in acetic anhydride (90 mL) was added with 70% nitric acid (0.38 mL, d=1.42) with stirring. After stirring for 2 hours, the mixture was added with water (100 mL), and the mixture was further stirred for 1 hour. The mixture was extracted by adding diethyl ether, and washed twice with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resultant mixture was purified by silica gel column chromatography (ethyl acetate:n-hexane=5:1 v/v) to obtain the title compound (0.38 g, 31%).

Workup

  1. stirringAfter stirring for 2 hours
  2. stirringthe mixture was further stirred for 1 hour
  3. extractionThe mixture was extracted
  4. additionby adding diethyl ether
  5. washwashed twice with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resultant mixture was purified by silica gel column chromatography (ethyl acetate:n-hexane=5:1 v/v)

Sources & evidence

ORD record
ord-8865674b028344d0bea1c99f203a3663
Source dataset
uspto-grants-2006_05
Patent number
US07045516B1

Reaction notes

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