Hydrochloric Acid → HCID 18630993, compound

HRID 1060005Notes

Reaction equation

HRID 1060005 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([CH:13]=[CH:14][C:15]#[N:16])=[C:11]([N+:19]([O-])=O)[CH:10]=2)[CH:4]=1.O.O.[Sn](Cl)[Cl:25].[ClH:27].C(=O)([O-])O.[Na+]>C(O)C.C(OCC)(=O)C.O1CCOCC1>[ClH:25].[ClH:27].[NH2:16][C:15]1[CH:14]=[CH:13][C:12]2[C:11](=[CH:10][C:9]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=3)=[CH:18][CH:17]=2)[N:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 54327211HCID 54327211, compound

Product 1

HCID 18630993HCID 18630993, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 4-(4-methoxypyridin-2-yl)-2-nitrocinnamonitrile (308 mg) in ethanol (30 ml) was added tin (II) chloride dihydrate (1.41 g), and the mixture was refluxed for 30 minutes. Then to the solution was added hydrochloric acid (12N, 5 ml), and the mixture was refluxed for 6 hours. After cooling, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 150 g, 10% methanol in dichloromethane). The compound obtained was dissolved in ethyl acetate, and a solution of hydrogen chloride in 1,4-dioxane (4N, 1 ml) was added. The precipitate was collected by filtration and dried to give 2-amino-7-(4-methoxypyridin-2-yl)-quinoline dihydrochloride (77 mg).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. temperaturethe mixture was refluxed for 6 hours
  3. temperatureAfter cooling
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography (silica gel 150 g, 10% methanol in dichloromethane)
  9. customThe compound obtained
  10. filtrationThe precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-889e8bce6d1b43309aef4c87588cb231
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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