Octane → HCID 23650206, compound

HRID 2238576Notes

Reaction equation

HRID 2238576 reaction equation
C(C(C)=O)C.O.[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16](=[O:33])[N:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:20]=1)#[N:8].[C:34]([OH:43])(=[O:42])[C@@H:35]([C@H:37]([C:39]([OH:41])=[O:40])[OH:38])[OH:36].CCCCCCCC>O1CCCC1>[C:39]([CH:37]([CH:35]([C:34]([OH:43])=[O:42])[OH:36])[OH:38])([OH:41])=[O:40].[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16](=[O:33])[N:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:20]=1)#[N:8]

Participants

6

Reactant 4

HCID 356OctaneHCID 6569Methyl Ethyl KetoneHCID 444305L-Tartaric acidHCID 68419241HCID 68419241, compound

Product 1

HCID 23650206HCID 23650206, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl ethyl ketone (7 mL) was added to 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate (258.17 mg, 0.71 mmol), and completely resolved under reflux by using oil bath. Then, tetrahydrofuran solution of L(+)-tartaric acid (6 mL, containing 0.77 mmol of tartaric acid) was added, and the heating of the oil bath was stopped. Then, n-octane (22 mL) was added to the mixture, solid was precipitated, and subsequently allowed to stand for about 13 hours and a half in the oil bath. The obtained solid was collected by filtration, washed by n-octane (small amount), dried under reduced pressure at 60° C., for about 5 hours to provide 283.86 mg of the title compound as white crystals.

Workup

  1. temperatureunder reflux
  2. temperaturethe heating of the oil bath
  3. customwas precipitated
  4. filtrationThe obtained solid was collected by filtration
  5. washwashed by n-octane (small amount)
  6. customdried under reduced pressure at 60° C., for about 5 hours

Sources & evidence

ORD record
ord-1e3050d69ef54514b46fc72cc8485648
Source dataset
uspto-grants-2010_05
Patent number
US07718807B2

Reaction notes

Loading…