8-Methylimidazo(1,2-a)pyridine → 8-Methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

HRID 2238645Notes

Reaction equation

HRID 2238645 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1>C(O)CCC.[Ni]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]2[CH:8]=[CH:9][N:10]=[C:3]12

Participants

4

Conditions

Temperature
65 °C

Procedure

1 g of 8-methylimidazo[1,2-a]pyridine [3-1] was dissolved in 20 mL of 1-butanol, and a catalytic amount of Raney nickel of was added thereto. The mixture was stirred under a hydrogen atmosphere (5 atmospheric pressure) at 65° C. for 4 days. After cooling the reaction mixture back to room temperature, the insolubles were filtered through celite, and washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 823.3 mg of 8-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [46-1].

Workup

  1. temperatureAfter cooling the reaction mixture back to room temperature
  2. filtrationthe insolubles were filtered through celite
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f3eeb8f5b18457c8a4ed2edf6b5570b
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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