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

HRID 1060009ノート

反応式

HRID 1060009 の反応式
[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

参加物

9

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f187048786764ac99758c75380598765
出典データセット
uspto-grants-2003_02
特許番号
US06521643B1

反応ノート

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