Benzyl Alcohol → HCID 23060716, compound

HRID 750170Notes

Reaction equation

HRID 750170 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([N:18]1[C:27]([C:28]([OH:30])=[O:29])=[C:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23](F)[CH:24]=2)[C:19]1=[O:38])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O>[CH2:11]([N:18]1[C:27]([C:28]([OH:30])=[O:29])=[C:26]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:24]=2)[C:19]1=[O:38])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23060561HCID 23060561, compound

Product 1

HCID 23060716HCID 23060716, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in oil, 400 mg) was added to benzyl alcohol (6 ml) under ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 30 min. To the reaction mixture was added 2-benzyl-6-fluoro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (310 mg) and the mixture was stirred at 120° C. for 6 hrs. To the reaction mixture were added water and 10% hydrochloric acid to acidify the aqueous layer of the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from diisopropyl ether-hexane and the crystals were collected by filtration. Recrystallization (ethyl acetate-hexane) gave the title compound (250 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 120° C. for 6 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was crystallized from diisopropyl ether-hexane
  8. filtrationthe crystals were collected by filtration
  9. customRecrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ffe8187811f2423693ed51ee4aee6d1f
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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