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

HRID 593363Notes

Reaction equation

HRID 593363 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([O:11]C(=O)C)[CH2:7][CH2:8][C:9]=2[CH:10]=1.[OH-].[Na+].CCCCCCC.C(OCC)(=O)C>CO.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([OH:11])[CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 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-OLYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of acetic acid 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl ester (1.57 g, 7.42 mmol) in methanol (35.7 ml) was treated with 1M sodium hydroxide (8.9 ml). The mixture was stirred at room temperature for 1.5 hours. The reaction was followed by TLC (silica gel, heptane: ethyl acetate=1:1; UV detection 254 nm). After completion, the reaction mixture was treated with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulphate, then evaporated leaving a dark red liquid (1.15 g, 91%) which crystallised on standing. Following NMR the product was pure enough for the next step of the synthesis; (calculated) C8H8ClNO [169.61]; (found) [M+H]+=170.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-0fd45fee51bb4036abcab90002729c7a
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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