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

HRID 1424225Notes

Reaction equation

HRID 1424225 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC(=O)C)(=O)C.[N+:23]([O-])([OH:25])=[O:24]>O>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[C:10]([N+:23]([O-:25])=[O:24])[CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic Anhydride2×HCID 15578623N-(4-cyclopentylphenyl)acetamide

Product 1

HCID 86699135N-(4-cyclopentyl-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of N-(4-cyclopentylphenyl)acetamide (Preparation 97, 18.5 g, 91.0 mmol) in acetic anhydride (148 mL, 1570 mmol) cooled in an ice/brine bath was added dropwise a solution of nitric acid (5.7 mL, 140 mmol) in acetic anhydride (40 mL, 400 mmol). After stirring for 4 hours, the reaction mixture was added water and extracted with methylene chloride (3×). The organic layers were combined, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. This provided product (19.48 g, 86%) as a brown oil that was used without further purification.

Workup

  1. temperaturecooled in an ice/brine bath
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis provided product (19.48 g, 86%) as a brown oil that was used without further purification

Sources & evidence

ORD record
ord-c62285406b51467cb73edab1bf4a15ac
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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