1,4-Cyclohexadiene → 2-(8-Hydroxy-2-methylimidazo[1,2-a]pyridin-3-yl)acetonitrile

HRID 544469Notes

Reaction equation

HRID 544469 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][C:20]#[N:21])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C1CC=CCC=1>[Pd].CN(C)C=O>[C:20]([CH2:19][C:15]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]2=[N:17][C:16]=1[CH3:18])#[N:21]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 108137Sch 28080

Product 1

HCID 133382662-(8-Hydroxy-2-methylimidazo[1,2-a]pyridin-3-yl)acetonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

8-Benzyloxy-3-cyanomethyl-2-methylimidazo[1,2-a]pyridine (40 g, 0.14 mol), 1,4-cyclohexadiene (50 g, 0.62 mol), dimethylformamide (600 ml) and palladium black (2 g) are stirred together and heated. At 45° C., asudden exotherm occurs and the temperature rises rapidly to 75°-80°. Heating is discontinued and the mixture stirred for1 hr. The catalyst is removed by filtration and the cyclohexadiene removed in vacuo. The dimethylformamide is removed in vacuo (0.1 mm) at 55°to afford 3-cyanomethyl-2-methyl-8-hydroxy imidazo[1,2-a]pyridine (27 g, 0.14 mol).

Workup

  1. temperatureheated
  2. customAt 45° C.
  3. customrises rapidly to 75°-80°
  4. temperatureHeating
  5. customThe catalyst is removed by filtration
  6. customthe cyclohexadiene removed in vacuo
  7. customThe dimethylformamide is removed in vacuo (0.1 mm) at 55°to

Sources & evidence

ORD record
ord-3a7ef4a3bdd44203aa43683ad674244f
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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