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

HRID 1060009노트

반응식

HRID 1060009 반응식
[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

참가 물질

9

반응물 3

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

생성물 1

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

시약·촉매·용매 5

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f187048786764ac99758c75380598765
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

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