Hydrogen Bromide → HCID 13051053, compound

HRID 1649012Notes

Reaction equation

HRID 1649012 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]2.[H-].[Na+].[CH3:24]I.[BrH:26]>CN(C)C=O.CC(C)=O>[BrH:26].[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:24])[C:16](=[O:21])[CH2:15][CH2:14]2

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13051062HCID 13051062, compound

Product 1

HCID 13051053HCID 13051053, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-(3-methylimidazo[1,2-a]-pyridine-2-yl)-3,4-dihydrocarbostyril (3 g) in dimethylformamide (50 ml) was added 50% oily sodium hydride (590 mg) and the mixture was reacted for 2 hours at room temperature. Then, after adding methyl iodide (1.85 g), the mixture was further reacted for 3 hours at room temperature. After completion of reaction, dimethylformamide was evaporated. Chloroform and 0.5 N sodium hydroxide were added to the residue for extraction. The chloroform layer was washed with water thoroughly and dried followed by evaporation of chloroform. The residue was purified using silica gel column chromatography and the oily product thus obtained was dissolved in acetone. The solution was adjusted to pH of about 1 by the addition of 48% hydrobromic acid and crystals which formed were collected by filtration. The crude crystals thus obtained were recrystallized from water to give 2.9 g of 6-(3-methylimidazo[1,2-a]pyridine-2-yl)-1-methyl-3,4-dihydrocarbostyril monohydrobromide.

Workup

  1. customthe mixture was reacted for 2 hours at room temperature
  2. customthe mixture was further reacted for 3 hours at room temperature
  3. customwas evaporated
  4. additionChloroform and 0.5 N sodium hydroxide were added to the residue for extraction
  5. washThe chloroform layer was washed with water thoroughly
  6. customdried
  7. customfollowed by evaporation of chloroform
  8. customThe residue was purified
  9. customthe oily product thus obtained
  10. customformed
  11. filtrationwere collected by filtration
  12. customThe crude crystals thus obtained
  13. customwere recrystallized from water

Sources & evidence

ORD record
ord-3a392b43d8d3416fae5573dc74f9df24
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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