Phenylacetyl chloride → HCID 5083474, compound

HRID 1896739Notes

Reaction equation

HRID 1896739 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12]1([CH2:18][C:19](Cl)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O1CCOCC1>[CH2:18]([C:19]1[O:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[N:1]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 14798Sodium HydroxideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 5083474HCID 5083474, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
210 °C

Procedure

To 2-amino-4-nitrophenol (300 mg, 1.95 mmol) in dioxane (2.5 mL) was added 2-phenylacetyl chloride (290 μL, 2.15 mmol) at room temperature. The reaction vessel was heated in the microwave at 210° C. for 15 min. After cooling, the mixture was slowly poured into 1M aqueous sodium hydroxide (50 mL), and the resulting precipitate filtered and washed with water. The resulting solid was purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 1:7 v/v to ethyl acetate/hexanes 1:5 v/v) to afford 165 mg (33%) of the title compound (LCMS RT=6.47 min, MH+ 255.2)

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate filtered
  3. washwashed with water
  4. customThe resulting solid was purified by column chromatography
  5. washeluting

Sources & evidence

ORD record
ord-f30616befb8f4243aec9a42715eb5103
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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