Hydrochloric Acid → HCID 70518419, compound

HRID 1649017Notes

Reaction equation

HRID 1649017 reaction equation
[N:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]2[C:13]=1[CH2:14][CH2:15][C:16](=[O:24])[NH:17]2)=[O:2].[ClH:25].O>CO.[C].[Pd]>[OH2:2].[ClH:25].[NH2:1][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]2[C:13]=1[CH2:14][CH2:15][C:16](=[O:24])[NH:17]2.[NH2:1][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]2[C:13]=1[CH2:14][CH2:15][C:16](=[O:24])[NH:17]2.[ClH:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13260283HCID 13260283, compound

Product 1

HCID 70518419HCID 70518419, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 5-(3-nitrosoimidazo[1,2-a]-pyridine-2-yl)-8-methoxy-3,4-dihydrocarbostyril (20.85 g) in methanol (500 ml) was added 12 ml of concentrated hydrochloric acid to render the suspension acidic. 10% Palladium-carbon (2 g), was added to the suspension, and catalytic reduction was carried out at room temperature under atmospheric pressure. After completion of reaction, water was added to the reaction mixture to dissolve and the resulting mixture was heated. After removing the catalyst by filtration, the filtrate was concentrated to dryness. Acetone was added to the residue, and crystals which precipitated were collected by filtration and recrystallized from water to give 21.20 g of 5-(3-aminoimidazo[1,2-a]pyridine-2-yl)-8-methoxy-3,4-dihydrocarbostyril monohydrochloride hemihydrate.

Workup

  1. customwas carried out at room temperature under atmospheric pressure
  2. additionwas added to the reaction mixture
  3. dissolutionto dissolve
  4. temperaturethe resulting mixture was heated
  5. customAfter removing the catalyst
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated to dryness
  8. additionAcetone was added to the residue, and crystals which
  9. customprecipitated
  10. filtrationwere collected by filtration
  11. customrecrystallized from water

Sources & evidence

ORD record
ord-b2a637d23033416bbfca338d5afbaef1
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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