Sodium borohydride → [6-(1H-Imidazol-1-yl)pyridin-3-yl]methanol

HRID 1031424Notes

Reaction equation

HRID 1031424 reaction equation
[BH4-].[Na+].[N:3]1([C:8]2[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][N:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1>CO.O>[N:3]1([C:8]2[CH:17]=[CH:16][C:11]([CH2:12][OH:13])=[CH:10][N:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 4315458methyl 6-(1H-imidazol-1-yl)nicotinate

Product 1

HCID 14207630[6-(1H-Imidazol-1-yl)pyridin-3-yl]methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

NaBH4 (37.82 g) is added portionwise to a suspension of the imidazolyl ester of Step 2. above (9.98 g) in methanol at about 0.° C. The reaction mixture is heated to reflux for 71/2 hours, allowed to cool and stand 15 hours. Water (75 ml) is added, and the quenched reaction mixture evaporated, affording a solid residue which is suspended in water, extracted with chloroform dried over Na2SO4, filtered and evaporated, recrystallized (CHCl3), affording the desired product as a white solid. M.P.=128.5°-130° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 71/2 hours
  3. temperatureto cool
  4. customthe quenched reaction mixture
  5. customevaporated
  6. customaffording a solid residue which
  7. extractionextracted with chloroform
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customrecrystallized (CHCl3)

Sources & evidence

ORD record
ord-7e8ddf07c3a64967b0a43b4e4f2eeb12
Source dataset
uspto-grants-1990_09
Patent number
US04954494

Reaction notes

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