Hydrochloric Acid → 1-(5-Chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane-1-ol

HRID 54513Notes

Reaction equation

HRID 54513 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)=[O:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:7]([OH:8])[CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 19959422HCID 19959422, compound

Product 1

HCID 199594181-(5-Chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7.8 g of 2-[2'-(1H-imidazol-1-yl)acetyl]-5-chloropyridine in 40 ml of methanol is charged at 0°, in portions, with 2.0 g of sodium borohydride. The mixture is stirred for one hour at 0°. For working-up the mixture is decomposed by careful addition of 1N hydrochloric acid at 0°, followed by 1N sodium hydroxide to reach a pH of 9. The solvents are evaporated in vacuo. The residue is stirred with water and dichloromethane, the aqueous phase is extracted twice with dichloromethane and the combined organic extracts are washed with brine, dried and evaporated. The compound is obtained as a cream coloured solid; m.p.: >210° (decomp.). Purification is possible by chromatography over silicagel.

Workup

  1. customThe solvents are evaporated in vacuo
  2. stirringThe residue is stirred with water and dichloromethane
  3. extractionthe aqueous phase is extracted twice with dichloromethane
  4. washthe combined organic extracts are washed with brine
  5. customdried
  6. customevaporated
  7. customThe compound is obtained as a cream
  8. customPurification

Sources & evidence

ORD record
ord-694c4c0705834ce681e468af2f405c02
Source dataset
uspto-grants-1997_04
Patent number
US05622982

Reaction notes

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