Ethanol → 5-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiophen-2-ylamine

HRID 853365

반응식

HRID 853365 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([N+:21]([O-])=O)=[CH:19][CH:20]=1.[Cl-].[NH4+].C(O)C.O>[Fe].CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([NH2:21])=[CH:19][CH:20]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 229368146,7-Dimethoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline

생성물 1

HCID 229363515-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiophen-2-ylamine수율 138.5%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

After suspending 6,7-dimethoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline (1.39 g, 4.00 mmol), iron (1.12 g, 20.0 mmol) and ammonium chloride (2.18 g, 40.0 mmol) in an ethanol (32 ml)—water (8 ml) mixed solvent, the suspension was heated and stirred at 80° C. for 5 minutes. After completion of the reaction, the reaction mixture was filtered with celite and washed in ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=3:1), and the fraction containing the target substance was concentrated to obtain the title compound (1.93 g, 5.54 mmol, 55%) as yellowish-brown crystals.

후처리

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe filtrate was distilled off under reduced pressure
  10. customThe obtained crude product
  11. additionthe fraction containing the target substance
  12. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-0fc2c1efa8ee4348a60493559544b334
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253286B2

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