Acetic Anhydride → 3-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

HRID 2409152Notes

Reaction equation

HRID 2409152 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[CH:7]=1.[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:15][CH:10]1[C:5]2[N:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=2[CH2:8][CH2:9]1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 580828393-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

Product 1

HCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl AcetateYield 71%

Procedure

A solution of 3-chloro-6,7-dihydro-5H-cyclopentapyridine 1-oxide (1 g, 5.9 mmole) in acetic anhydride (30 ml) was heated to 110° C. and stirred at this temperature for 20 h. The solvent was evaporated and the residue was partitioned between aqueous saturated NaHCO3 solution and dichloromethane. The organic layer was dried, evaporated and the residue was purified by flash chromatography over silica using EtOAc/n-heptane (gradient from 0% to 30% EtOAc) to give the title compound as a red liquid (880 mg, 71% yield). MS (ESI): m/z=212.0 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between aqueous saturated NaHCO3 solution and dichloromethane
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was purified by flash chromatography over silica

Sources & evidence

ORD record
ord-39131da47a5749b8a69f5a6f50f6c980
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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