Ammonium formate → HCID 178505673, compound

HRID 1756143Notes

Reaction equation

HRID 1756143 reaction equation
C([N:8]1[C:12]([C:13]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)(O)[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:11][N:10]=[CH:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH:13]([C:12]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 19916873HCID 19916873, compound

Product 1

HCID 178505673HCID 178505673, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1-benzyl-5-[1,4-bis(4-fluorophenyl)-1-hydroxybutyl]-1H-imidazole (10 g) is dissolved in conc. acetic acid (100 ml). Into the solution is added 0,1 g of palladium on carbon and 0,8 g of ammoniumformate. The mixture is refluxed for an hour and cooled to room temperature. The solution is filtered through silicous earth. The acetic acid filtrate is evaporated, the residue is dissolved in methylene chloride and washed once with 2M aqueous sodium hydroxide solution and once with water. The methylene chloride solution is dried with sodium sulphate and evaporated under reduced pressure. The product is then made to hydrochloride salt with dry hydrogen chloride in diethylether. M.p. 135°-137° C.

Workup

  1. temperatureThe mixture is refluxed for an hour
  2. filtrationThe solution is filtered through silicous earth
  3. customThe acetic acid filtrate is evaporated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washwashed once with 2M aqueous sodium hydroxide solution and once with water
  6. dry with materialThe methylene chloride solution is dried with sodium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ac81da6255c84ebd8373bc6fa933f243
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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