Acetone → HCID 12445549, compound

HRID 614341Notes

Reaction equation

HRID 614341 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[NH:10][C:9]2=[O:17])[N:3]=1.[CH3:18][C:19]([CH3:21])=O.[OH-].[K+].C(Br)C=C>O>[CH2:21]([N:10]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:8]([C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=2)[C:9]1=[O:17])[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 124455433-(6-Methylpyridin-2-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 12445549HCID 12445549, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1 g. of 1,3-dihydro-3-(2-methylpyridin-6-yl)imidazo[4,5-b]pyridin-2-one in 100 ml. of acetone and 450 mg. of powdered potassium hydroxide was stirred 10 minutes and 1.1 g. of allyl bromide was added. After refluxing for 1.5 hours, the mixture was allowed to stand overnight at room temperature. The mixture was diluted with water and the acetone was evaporated causing crystallization of 325 mg. of 1-allyl-1,3-dihydro-3-(2-methylpyridin-6yl)imidazo[4,5-b]pyridin-2-one, m.p. 111°-112° C.

Workup

  1. additionA mixture of 1 g
  2. temperatureAfter refluxing for 1.5 hours
  3. customthe acetone was evaporated
  4. customcrystallization of 325 mg

Sources & evidence

ORD record
ord-273c4447f87d4ea0b57fd7e3de4d1022
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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