8-(Benzyloxy)-2-methylimidazo[1,2-a]pyridine → 2-Methyl-6,7-dihydroimidazo[1,2-a]pyridin-8(5H)-one

HRID 723398Notes

Reaction equation

HRID 723398 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([CH:15]=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>CO>[CH3:18][C:16]1[N:17]=[C:10]2[C:9](=[O:8])[CH2:14][CH2:13][CH2:12][N:11]2[CH:15]=1

Participants

4

Reactant 2

HCID 139003368-(Benzyloxy)-2-methylimidazo[1,2-a]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 120824682-Methyl-6,7-dihydroimidazo[1,2-a]pyridin-8(5H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

60 g (251.8 mmol) of 8-benzyloxy-2-methylimidazo[1,2-a]pyridine (Kaminski et al, J. Med. Chem. 1985, 28, 876–892) are hydrogenated on Pd-carbon in 400 ml of methanol at a hydrogen pressure of 55 bar and 70° C. After completion of the hydrogenation, the catalyst is filtered off and the filtrate is concentrated. The residue (38 g) is taken up in dichloromethane and the solution is treated in portions at room temperature with manganese dioxide (109.5 g). The reaction mixture is stirred at room temperature for 22 h and then filtered through silica gel. The filtrate is concentrated to a residue and the crystallizate is dried in vacuo at 60° C. 25.13 g (66% of theory) of the title compound are obtained.

Workup

  1. filtrationAfter completion of the hydrogenation, the catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. additionthe solution is treated in portions at room temperature with manganese dioxide (109.5 g)
  4. filtrationfiltered through silica gel
  5. concentrationThe filtrate is concentrated to a residue
  6. customthe crystallizate is dried in vacuo at 60° C

Sources & evidence

ORD record
ord-a5a531df358445b28570c2de2b13307e
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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