Acetic Anhydride → N-(4-cyclopentylphenyl)acetamide

HRID 1424233Notes

Reaction equation

HRID 1424233 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C2C=CC=CC=2[N+]([O-])=O)CCCC1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>CO.[Pd]>[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:29](=[O:31])[CH3:30])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 120656691-Cyclopentyl-4-nitrobenzeneHCID 570407321-Cyclopentyl-2-nitrobenzene

Product 1

HCID 15578623N-(4-cyclopentylphenyl)acetamideYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-cyclopentyl-4-nitrobenzene and 1-cyclopentyl-2-nitrobenzene (Preparation 96, 28.92 g, 151.2 mmol) in methanol (300 mL) was added acetic anhydride (20.1 mL, 213 mmol) and palladium (2 g, 20 mmol) (10% on carbon, Degussa type) and the reaction mixture hydrogenated at a pressure of 40 psi for 5 hours. The mixture was filtered through celite concentrated in vacuo, and purified by silica gel column chromatography eluting with a 0-50% ethyl acetate/hexanes gradient. The isomers separated at this stage to give (16.52 g, 54%) of product as a brown solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel column chromatography
  4. washeluting with a 0-50% ethyl acetate/hexanes gradient
  5. customThe isomers separated at this stage

Sources & evidence

ORD record
ord-12f810bc0dd7494289ceccdc230299cd
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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