Chloroacetyl chloride → 2-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide

HRID 576071Notes

Reaction equation

HRID 576071 reaction equation
C(=O)([O-])O.[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[OH:16].[Cl:17][CH2:18][C:19](Cl)=[O:20].[Cl-].[NH4+]>C(OCC)(=O)C.O>[Cl:17][CH2:18][C:19]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[OH:16])=[O:20]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 51272912-Amino-6-nitrophenol

Product 1

HCID 136462502-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydrogen carbonate (6.30 g, 75.0 mmol) and water (75 mL) were added to a solution of 2-amino-6-nitrophenol obtained (5.77 g, 37.5 mmol) in ethyl acetate (75 mL) while cooling in ice, and chloroacetic acid chloride (3.58 mL, 45.0 mmol) was added dropwise thereto. After stirring at room temperature for 1.5 hr, the reaction mixture was cooled in ice, saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1) to afford 2-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide as a pale yellow powder (5.70 g).

Workup

  1. temperaturewhile cooling in ice
  2. temperaturethe reaction mixture was cooled in ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1)

Sources & evidence

ORD record
ord-e59b37f77a854fafa3db8bf8f9641c23
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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