Butyl bromide → HCID 21329306, compound

HRID 614347Notes

Reaction equation

HRID 614347 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[NH:12][C:11]3=[O:19])=[CH:4][C:3]=2[O:2]1.[OH-].[K+].Br[CH2:23][CH2:24][CH2:25][CH3:26]>CC(C)=O>[CH2:23]([N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[C:11]1=[O:19])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 119617392H-Imidazo[4,5-b]pyridin-2-one, 3-(1,3-benzodioxol-5-yl)-1,3-dihydro-

Product 1

HCID 21329306HCID 21329306, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2.6 g. (0.01 mole) of 1,3-dihydro-3-(3,4-methylenedioxyphenyl)imidazo[4,5-b]-pyridin-2-one in 150 ml. of acetone, was added 1.12 g. (0.02 mole) of powdered potassium hydroxide. The mixture was stirred at room temperature for 20 minutes and 2.74 g. (0.02 mole) of 1-bromobutane was added. The mixture was stirred at reflux for 16 hours and then evaporated in vacuo. The residue was extracted with a solution of 20 ml. of 2.5 N sodium hydroxide and 50 ml. of water. The product was separated by filtration and was purified by crystallization from ether-petroleum ether giving 2.4 g. of white needles melting at 74°-75° C.

Workup

  1. additionTo a suspension of 2.6 g
  2. stirringThe mixture was stirred
  3. temperatureat reflux for 16 hours
  4. customevaporated in vacuo
  5. extractionThe residue was extracted with a solution of 20 ml
  6. customThe product was separated by filtration
  7. customwas purified by crystallization from ether-petroleum ether giving 2.4 g

Sources & evidence

ORD record
ord-c3ca62fefccb47778086dfc0f31d5ffc
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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