Nitric Acid → N-(4-Neopentyl-2-nitrophenyl)acetamide

HRID 1424226Notes

Reaction equation

HRID 1424226 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)[C:2]([CH3:5])([CH3:4])[CH3:3].[N+:16]([O-])([OH:18])=[O:17].O>C(OC(=O)C)(=O)C>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 825793N-[4-(2,2-dimethylpropyl)phenyl]acetamide

Product 1

HCID 85802767N-(4-Neopentyl-2-nitrophenyl)acetamideYield 97%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

To a suspension of N-(4-neopentylphenyl)acetamide (Preparation 98, 2.54 g, 12.4 mmol) in acetic anhydride (20 mL) cooled in an ice bath was added a solution of nitric acid (0.78 mL, 18 mmol) in acetic anhydride (5 mL) dropwise. The solution was allowed to warm to room temperature for 18 hours. The yellow solution was added to water and extracted with dichloromethane (3×). The organic layers were dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with a 0-50% ethyl acetate/hexanes gradient to provide the title compound (3.0 g, 97%) as a yellow oil.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialThe organic layers were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. washeluting with a 0-50% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-7f6800975b5748f4973f0e5db95c8a63
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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