Sodium borohydride → 2-Methylimidazo[1,2-a]pyridine-8-methanol

HRID 544474Notes

Reaction equation

HRID 544474 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH:10]=[O:11])=[CH:8][CH:7]=[CH:6][N:5]2[CH:12]=1.[BH4-].[Na+]>C(O)(C)C>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][N:5]2[CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 13900241HCID 13900241, compound

Product 1

HCID 139003302-Methylimidazo[1,2-a]pyridine-8-methanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred suspension of 56.8 g (0.36 mol) 2-methyl-8-formylimidazo[1,2-a]pyridine in 400 ml isopropanol at 0°is added in portions 8 g (0.21 mol) sodium borohydride. The reaction mixture is stirred at room temperature for an additional 2 hours. The excess sodium borohydride is decomposed by the addition of distilled waterand the solution concentrated under reduced pressure at 50° C. The residue is dissolved in water and extracted with chloroform. The chloroform extracts are combined and dried over anhydrous sodium sulfate. Following filtration, the chloroform is removed under reduced pressure to give 2-methyl-8-hydroxymethylimidazo[1,2-a]pyridine.

Workup

  1. concentrationconcentrated under reduced pressure at 50° C
  2. dissolutionThe residue is dissolved in water
  3. extractionextracted with chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltration
  6. customthe chloroform is removed under reduced pressure

Sources & evidence

ORD record
ord-0cd4031f60504719a0755472e7bc360a
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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