Hydrochloric Acid → HCID 20481492, compound

HRID 1649022Notes

Reaction equation

HRID 1649022 reaction equation
[N:1]1[C:2]([C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]3[C:11]=2[CH2:12][CH2:13][C:14](=[O:22])[NH:15]3)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(C1C(=O)C([Cl:33])=C(Cl)C(=O)C=1C#N)#N.O1CCOCC1.Cl>CC(C)=O>[OH2:20].[ClH:33].[N:1]1[C:2]([C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]3[C:11]=2[CH:12]=[CH:13][C:14](=[O:22])[NH:15]3)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 13260279HCID 13260279, compound

Product 1

HCID 20481492HCID 20481492, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-(Imidazo[1,2-a]pyridine-2-yl)-8-methoxy-3,4-dihydrocarbostyril (1.4 g) and DDQ (3.5 g) were added to dioxane (30 ml) and the mixture was refluxed for 5 hours. The reaction mixture was concentrated under reduced pressure and the residue was extracted by the addition of chloroform and 0.5 N sodium hydroxide. The chloroform layer was washed with 0.5 N sodium hydroxide and then with water twice. After drying, chloroform was evaporated. The residue was isolated and purified through a silica gel column. The crude crystals thus obtained were dissolved in acetone and hydrochloric acid was added to the resulting solution. Crystals which precipitated were collected by filtration and recrystallized from water to give 410 mg of 5-(imidazo[1,2-a]-pyridine-2-yl)-8-methoxycarbostyril monohydrochloride monohydrate.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe residue was extracted by the addition of chloroform and 0.5 N sodium hydroxide
  4. washThe chloroform layer was washed with 0.5 N sodium hydroxide
  5. customAfter drying
  6. customchloroform was evaporated
  7. customThe residue was isolated
  8. custompurified through a silica gel column
  9. customThe crude crystals thus obtained
  10. customCrystals which precipitated
  11. filtrationwere collected by filtration
  12. customrecrystallized from water

Sources & evidence

ORD record
ord-7f394a7e869845c0a65150d883230478
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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