Nitric Acid → N-(2-nitro-4-(oxetan-3-yl)phenyl)acetamide

HRID 511665

Reaction equation

HRID 511665 reaction equation
[N+:1]([O-:4])(O)=[O:2].[O:5]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)[CH2:6]1.[N+]([O-])(O)=O.C(Cl)Cl.[NH4+].[OH-]>C(Cl)Cl>[N+:1]([C:11]1[CH:10]=[C:9]([CH:7]2[CH2:8][O:5][CH2:6]2)[CH:14]=[CH:13][C:12]=1[NH:15][C:16](=[O:18])[CH3:17])([O-:4])=[O:2]

Participants

6

Reactant 4

HCID 944Nitric Acid2×HCID 14923Ammonium HydroxideHCID 20264123HNO3 dichloromethaneHCID 67776166N-(4-(Oxetan-3-YL)phenyl)acetamide

Product 1

HCID 67776164N-(2-nitro-4-(oxetan-3-yl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The organic phase (upper phase) was isolated and the process was repeated with an additional 20 ml CH2Cl2. The organic extracts were combined, it was assumed the organic phase contained about 5 g (−80 mmol) of anhydrous HNO3. Using a 50 fold excess, this required about 25 ml of solution. The nitric acid solution was cooled in a ice bath. The N-(4-oxetan-3-ylphenyl)acetamide (21 0 mg, 0.70 mmol) was treated with 25 ml of the chilled HNO3/CH2Cl2 solution and was allowed to stir about 30 minutes. The reaction mixture was carefully poured into 45 ml 1 0% NH4OH solution and carefully shaken. The phases were separated and the aqueous phase was washed with 20 ml CH2Cl2. The combined organic phase was dried over Na2SO4, filtered and concentrated. The crude material was purified

Workup

  1. customThe organic phase (upper phase) was isolated
  2. stirringcarefully shaken
  3. customThe phases were separated
  4. washthe aqueous phase was washed with 20 ml CH2Cl2
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified

Sources & evidence

ORD record
ord-e1917049c81346c38e02a6ec24682373
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Linked notes

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