Hydrochloric Acid → HCID 13260225, compound

HRID 1649011Notes

Reaction equation

HRID 1649011 reaction equation
[N:1]1[C:2]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]3)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(C1C(=O)C([Cl:31])=C(Cl)C(=O)C=1C#N)#N.Cl>O1CCOCC1.CC(C)=O>[ClH:31].[N:1]1[C:2]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]3)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13051054HCID 13051054, compound

Product 1

HCID 13260225HCID 13260225, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 6-(imidazo[1,2-a]pyridine-2-yl)-3,4-dihydrocarbostyril (5 g) in dioxane (50 ml) was added DDQ (6.47 g) with stirring at 70° C. The reaction mixture was heated for 5 hours with stirring. After completion of reaction, the solvent was evaporated. 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, washed with water and dried. After evaporating chloroform, the residue obtained was isolated and purified using silica gel column chromatography. Oily product obtained was dissolved in acetone and the solution was adjusted to pH of about 1 with concentrated hydrochloric acid. Crystals which formed were collected by filtration. The crude crystals thus obtained were recrystallized from water to give 2.4 g of 6-(imidazo[1,2-a]pyridine-2-yl)carbostyril monohydrochloride.

Workup

  1. temperatureThe reaction mixture was heated for 5 hours
  2. stirringwith stirring
  3. customAfter completion of reaction
  4. customthe solvent was evaporated
  5. extractionThe residue was extracted by the addition of chloroform and 0.5 N sodium hydroxide
  6. washThe chloroform layer was washed with 0.5 N sodium hydroxide
  7. washwashed with water
  8. customdried
  9. customAfter evaporating chloroform
  10. customthe residue obtained
  11. customwas isolated
  12. custompurified
  13. customOily product obtained
  14. customCrystals which formed
  15. filtrationwere collected by filtration
  16. customThe crude crystals thus obtained
  17. customwere recrystallized from water

Sources & evidence

ORD record
ord-7f52a92375a54a249a6cd1ae81c1cffe
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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