Hydrochloric Acid → 7-(4-Methoxypyridin-2-yl)-2-methylaminoquinoline dihydrochloride

HRID 1060013Notes

Reaction equation

HRID 1060013 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:10]=2)[N:5]=1.[ClH:22]>CO.C(OCC)(=O)C.O1CCOCC1>[ClH:3].[ClH:22].[CH3:21][O:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([CH:12]=[CH:13][C:4]([NH:2][CH3:1])=[N:5]3)=[CH:10][CH:9]=2)[CH:19]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 18667574HCID 18667574, compound

Product 1

HCID 186675287-(4-Methoxypyridin-2-yl)-2-methylaminoquinoline dihydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methylamine in methanol (40% w/w, 5 ml) was added 2-chloro-7-(4-methoxypyridin-2-yl)quinoline (140 mg). The mixture was heated in a steel autoclave at 120° C. for 16 hours. After cooling, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, 5% 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 7-(4-methoxypyridin-2-yl)-2-methylaminoquinoline dihydrochloride (106 mg).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel 25 g, 5% methanol in dichloromethane)
  4. customThe compound obtained
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-0fbbbd771b704f97842926c18ea1c995
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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