HCID 15790517, compound → HCID 15790527, compound

HRID 235054Notes

Reaction equation

HRID 235054 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:13]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][NH:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 15790517HCID 15790517, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15790527HCID 15790527, compoundYield 117.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.495 g (5.2 mmol) of N-(4-pyridyl)-4-biphenyl-acetamide in 30 mL of THF was added dropwise to a rapidly stirred suspension of 0.49 g of lithium aluminum hydride (13 mmol) in 30 mL of THF at room temperature. Once the addition was complete, the mixture was heated to reflux and was refluxed for approximately 17 hours. The mixture was then cooled in an ice bath and quenched by the dropwise addition of 30 mL of saturated ammonium chloride followed by 2 mL of 15% sodium hydroxide. The mixture was filtered and the phases separated. The aqueous phase was extracted with ethyl ether (2×75 mL). The combined organic phases were then dried, filtered, and concentrated to give 1.68 g of a yellow solid. This was chromatographed on silica gel, eluting with 90% CHCl3 /10% CH3OH. Removal of solvent left 1.20 g. of a light yellow solid. This was recrystallized from hexane/ethyl acetate and vacuum oven dried to give 0.773 g of a very light yellow solid. M.P. 140.0° C.

Workup

  1. additionOnce the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. temperaturewas refluxed for approximately 17 hours
  5. temperatureThe mixture was then cooled in an ice bath
  6. customquenched by the dropwise addition of 30 mL of saturated ammonium chloride
  7. filtrationThe mixture was filtered
  8. customthe phases separated
  9. extractionThe aqueous phase was extracted with ethyl ether (2×75 mL)
  10. customThe combined organic phases were then dried
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-23ed310a749842e389764dca0f6ded6d
Source dataset
uspto-grants-1997_01
Patent number
US05597836

Reaction notes

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