Sodium Hydroxide → 3-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL

HRID 2409153Notes

Reaction equation

HRID 2409153 reaction equation
C([O:4][CH:5]1[C:13]2[N:12]=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[CH2:7][CH2:6]1)(=O)C.[OH-].[Na+]>CO.O>[Cl:14][C:10]1[CH:11]=[N:12][C:13]2[CH:5]([OH:4])[CH2:6][CH2:7][C:8]=2[CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

Product 1

HCID 580828163-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 3-chloro-6,7-dihydro-5H-cyclopentapyridin-7-yl acetate (1.57 g, 7.42 mmole) in MeOH (36 ml) was added aqueous NaOH solution (1M, 8.9 ml, 8.9 mmole) and the mixture was stirred at 22° C. for 1.5 h. The mixture was diluted with water and extracted with dichloromethane, the organic layer was dried and evaporated to give the title compound as a dark red liquid which crystallized on standing. MS (ESI): m/z=170.1 [M+H]+.

Workup

  1. extractionextracted with dichloromethane
  2. customthe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-4c13d00f5c214556828c2003e9b22f83
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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