Hydrochloric Acid → 2-Amino-3-methyl-7-(4-methylpyridin-2-yl)quinoline dihydrochloride

HRID 1060015Notes

Reaction equation

HRID 1060015 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]=[C:13]([CH3:16])[C:14]#[N:15])=[C:10]([N+:19]([O-])=O)[CH:9]=2)[CH:3]=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].[NH2:15][C:14]1[C:13]([CH3:16])=[CH:12][C:11]2[C:10](=[CH:9][C:8]([C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=3)=[CH:18][CH:17]=2)[N:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 536430862-(4-(4-Methylpyridin-2-yl)-2-nitrobenzylidene)propionitrile

Product 1

HCID 186309892-Amino-3-methyl-7-(4-methylpyridin-2-yl)quinoline dihydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2-(4-(4-methylpyridin-2-yl)-2-nitrobenzylidene)-propionitrile (221 mg) in ethanol (30 ml) was added tin (II) chloride dihydrate (1.25 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 25 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-3-methyl-7-(4-methylpyridin-2-yl)quinoline dihydrochloride (57 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 25 g, 10% methanol in dichloromethane)
  9. customThe compound obtained
  10. filtrationThe precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-31effa9719014d94aff7b5bdd65d3707
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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