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

HRID 1060009Notes

Reaction equation

HRID 1060009 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:17]=[CH:16][C:11]([CH:12]=[CH:13][C:14]#[N:15])=[C:10]([N+:18]([O-])=O)[CH:9]=2)[CH:3]=1.C(=O)([O-])O.[Na+].[ClH:26]>C(O)(=O)C.CN(C)C=O.C(OCC)(=O)C.O1CCOCC1.[Fe]>[ClH:26].[ClH:26].[NH2:15][C:14]1[CH:13]=[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:17][CH:16]=2)[N:18]=1

Participants

9

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 545662564-(4-Methylpyridin-2-yl)-2-nitrocinnamonitrile

Product 1

HCID 186674862-Amino-7-(4-methylpyridin-2-yl)quinoline dihydrochloride

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4-(4-methylpyridin-2-yl)-2-nitrocinnamonitrile (1.32 g) in acetic acid (5 ml) and N,N-dimethylformamide (5 ml) was added iron powder (1.63 g), and the mixture was stirred at 100° C. for 3 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 50 g, 5-10% 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-methylpyridin-2-yl)quinoline dihydrochloride (482 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 50 g, 5-10% methanol in dichloromethane)
  7. customThe compound obtained
  8. filtrationThe precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-f187048786764ac99758c75380598765
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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