Sodium Hydroxide → 5-{2-[5-Chloro-2-(4-chlorobenzyloxy)-phenyl]-cyclopent-1-enyl}-nicotinic Acid

HRID 1767198Notes

Reaction equation

HRID 1767198 reaction equation
C([O:3][C:4](=[O:32])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+]>CO.O.C(O)(=O)C>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[C:16]([C:12]2[CH2:13][CH2:14][CH2:15][C:11]=2[C:9]2[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=2)[C:4]([OH:32])=[O:3])[CH:21]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 588876485-{2-[5-Chloro-2-(4-chlorobenzyloxy)-phenyl]-cyclopent-1-enyl}-nicotinic Acid Ethyl Ester

Product 1

HCID 101513675-{2-[5-Chloro-2-(4-chlorobenzyloxy)-phenyl]-cyclopent-1-enyl}-nicotinic AcidYield 88.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-{2-[5-Chloro-2-(4-chlorobenzyloxy)-phenyl]-cyclopent-1-enyl}-nicotinic acid ethyl ester (90 mg) was hydrolysed in methanol (3 mL) and 2N sodium hydroxide (2 mL) at 60° C. with stirring for 2 hrs. The reaction mixture was then reduced down to ˜1 mL, diluted with water (10 mL) and treated with a few drops of glacial acetic acid to make the solution ˜pH5. The product was then extracted twice with dichloromethane (10 mL) dried (magnesium sulphate), and evaporated to give the title compound (75 mg).

Workup

  1. extractionThe product was then extracted twice with dichloromethane (10 mL)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated

Sources & evidence

ORD record
ord-845d55980a63435a86c9cb3007cb2e6d
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

Loading…