Acetic Acid → HCID 21936423, compound

HRID 1181392Notes

Reaction equation

HRID 1181392 reaction equation
[BH4-].[Na+].C(O)(=O)C.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=O)=[CH:16][N:15]=2)=[CH:10][CH:9]=1>O1CCOCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[CH:16][C:17]([CH2:18][NH2:20])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 69522758HCID 69522758, compound

Product 1

HCID 21936423HCID 21936423, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To an ice-bath cooled solution of sodium borohydride (5.47 g, 144.5 mmol) in anhydrous 1,4-dioxane (100 ml) was added slowly a solution of glacial acetic acid (8.27 ml, 144.5 mmol) in 1,4-dioxane (50 ml). To this mixture was added 6-(4-fluorophenyl)nicotinamide (Description 24; 6.25 g, 28.9 mmol) and the resulting mixture heated at reflux for 4 hours. The cooled reaction mixture was evaporated and water (60 ml) added slowly. This mixture was extracted with dichloromethane, and the solid which appeared between the layers was removed by filtration. This solid was triturated with a mixture of dichloromethane and iso-hexanes, filtered and dried to give the title compound (510 mg, 8%) as a pale green solid.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 4 hours
  3. customThe cooled reaction mixture
  4. customwas evaporated
  5. additionwater (60 ml) added slowly
  6. extractionThis mixture was extracted with dichloromethane
  7. customwas removed by filtration
  8. customThis solid was triturated with a mixture of dichloromethane and iso-hexanes
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-58bb4f3cc5464cdab07e4a780b5e0c29
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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