Hydrochloric Acid → HCID 68884056, compound

HRID 1294312Notes

Reaction equation

HRID 1294312 reaction equation
[CH3:1][C:2]1OC(C2C=CC=CC=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([CH2:21][O:22][C:23]2[C:28]([CH2:29][C:30]#N)=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:17][CH:16]=1.[CH2:32]([OH:34])[CH3:33].[OH-:35].[Na+].Cl.[OH2:38]>>[CH3:1][C:2]1[O:34][C:32]([C:33]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([CH2:21][O:22][C:23]2[C:28]([CH2:29][C:30]([OH:38])=[O:35])=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68886127HCID 68886127, compound

Product 1

HCID 68884056HCID 68884056, compoundYield 90%

Procedure

To a mixture of 2-[2-[[6-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridyl]methoxy]-3-pyridyl]acetonitrile (1.70 g) and ethanol (10 mL) was added a 2N aqueous sodium hydroxide solution (10 mL) and the mixture was heated under reflux for 17 hrs. 1N Hydrochloric acid (20 mL) and water were added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals (1.60 g, 90%) of 2-[2-[[6-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridyl]methoxy]-3-pyridyl]acetic acid. Recrystallization from ethyl acetate gave colorless prism crystals. melting point: 147-148° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8cb7330eb825434481b8e68f81a985c2
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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