Hydrochloric Acid → HCID 68886211, compound

HRID 1294341Notes

Reaction equation

HRID 1294341 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:25]=[CH:24][C:12]([CH2:13][O:14][C:15]3[C:20]([CH2:21][C:22]#N)=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:5][N:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[N:3]=1.C(O)C.[OH-:35].[Na+].Cl.[OH2:38]>>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:25]=[CH:24][C:12]([CH2:13][O:14][C:15]3[C:20]([CH2:21][C:22]([OH:38])=[O:35])=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:5][N:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[N:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68885708HCID 68885708, compound

Product 1

HCID 68886211HCID 68886211, compoundYield 74%

Procedure

To a mixture of 2-[2-[4-[[3-methyl-1-(2-pyridyl)-1H-pyrazol-4-yl]methoxy]benzyloxy]-3-pyridyl]acetonitrile (0.30 g) and ethanol (15 mL) was added a 2N aqueous sodium hydroxide solution (10 mL) and the mixture was heated under reflux for 24 hrs. 1N Hydrochloric acid (20 mL) and water were added to the reaction mixture. The precipitated crystals were collected by filtration and dried with air to give crystals (0.23 g, 74%) of 2-[2-[4-[[3-methyl-1-(2-pyridyl)-1H-pyrazol-4-yl]methoxy]benzyloxy]-3-pyridyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 150-151° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hrs
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried with air

Sources & evidence

ORD record
ord-9703934460294cdf9daf92f19f0d7350
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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