2-(N-chloroacetyl-2,6-dimethylphenylamino)cyclopentanol → HCID 12491483, compound

HRID 46573Notes

Reaction equation

HRID 46573 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][CH2:15][C:16]([N:18]([C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:32])[CH:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[OH:24])=[O:17]>CC(C)=O>[Cl:14][CH2:15][C:16]([N:18]([C:25]1[C:26]([CH3:32])=[CH:27][CH:28]=[CH:29][C:30]=1[CH3:31])[CH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=[O:24])=[O:17]

Participants

4

Reactant 2

HCID 155806532-(N-chloroacetyl-2,6-dimethylphenylamino)cyclopentanolHCID 131709961Jones' reagent

Product 1

HCID 12491483HCID 12491483, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 4.5-ml (0.004-mol) sample of Jones Reagent (26.72 g chromium trioxide in 23 ml of concentrated sulfuric acid diluted with H2O to 100 ml) was added dropwise to a vigorously stirred solution of 4.4 g (0.016 mol) 2-(N-chloroacetyl-2,6-dimethylphenylamino)cyclopentanol in 100 ml acetone. The acetone solution was decanted from the solids, dried over magnesium sulfate, treated with silica and evaporated under reduced pressure to give 3.7 g of pale yellow oil. The oil was chromatographed on silica gel using mixtures of ethyl ether/hexane as eluant. 2-(N-chloroacetyl-2,6-dimethylphenylamino)cyclopentanone was eluted with 25% ethyl ether/hexane, as a white solid. This product melted at 79°-82° C. after recrystallization from hexane. This product is tabulated in Table I, as Compound No. 1-A.

Workup

  1. customThe acetone solution was decanted from the solids
  2. dry with materialdried over magnesium sulfate
  3. additiontreated with silica
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a3be81916f264966bddaefcb92c62159
Source dataset
uspto-grants-1979_11
Patent number
US04174210

Reaction notes

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