Nitric Acid → N-(5-Acetyl-2-nitrophenyl)acetamide

HRID 1919611Notes

Reaction equation

HRID 1919611 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.[C:12]([C:15]1[CH:16]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=1)(=[O:14])[CH3:13]>ClCCl>[C:12]([C:15]1[CH:20]=[CH:19][C:18]([N+:1]([O-:4])=[O:2])=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:16]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 3462023'-Acetamidoacetophenone

Product 1

HCID 15276728N-(5-Acetyl-2-nitrophenyl)acetamideYield 20.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fuming white nitric acid (3.6 g) was added dropwise to acetic anhydride (12 ml) at 0° C. and stirred for 15 minutes. The N-(3-acetyl-phenyl)-acetamide (2 g; 11.3 mmol) was then added portionwise and the reaction mixture allowed to warm to room temperature. After stirring at room temperature for 15 minutes, the reaction mixture was poured onto ice (200 ml). Dichloromethane (200 ml) was added and the organic layer was separated, dried (magnesium sulphate), filtered and evaporated to give the crude residue. This was purified by column chromatography to give N-(5-acetyl-2-nitro-phenyl)-acetamide (515 mg), which was directly hydrolysed by heating in 6M hydrochloric acid (15 ml) at 80° C. for 2 hours. The cooled reaction mixture was basified using saturated sodium bicarbonate solution and then extracted into ethyl acetate (6×30 ml). The organic layers were dried (magnesium sulphate), filtered and evaporated to give the crude residue. This was purified by column chromatography (50% ethyl acetate in heptane) to give 3-amino-4-nitroacetophenone (226 mg, 11%).

Workup

  1. stirringAfter stirring at room temperature for 15 minutes
  2. additionthe reaction mixture was poured onto ice (200 ml)
  3. customthe organic layer was separated
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude residue
  8. customThis was purified by column chromatography

Sources & evidence

ORD record
ord-fa444d310e63414ab98c209cc659a062
Source dataset
uspto-grants-2012_05
Patent number
US08168653B2

Reaction notes

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