Stannous Chloride → 7-Amino-3-iodo-8-methoxy-2-phenyl-chromen-4-one

HRID 1037370노트

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HRID 1037370 반응식
[I:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([O:16][CH3:17])[C:7]([N+:13]([O-])=O)=[CH:8][CH:9]=2)[O:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl[Sn]Cl>C(OCC)(=O)C>[NH2:13][C:7]1[C:6]([O:16][CH3:17])=[C:5]2[C:10]([C:11](=[O:12])[C:2]([I:1])=[C:3]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:4]2)=[CH:9][CH:8]=1

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 670678843-Iodo-8-methoxy-7-nitro-2-phenyl-chromen-4-one

생성물 1

HCID 670677907-Amino-3-iodo-8-methoxy-2-phenyl-chromen-4-one수율 91.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a suspension of 3-iodo-8-methoxy-7-nitro-2-phenyl-chromen-4-one (903 mg, 2.1 mmol) in ethyl acetate (7 mL) and IMS (7 mL) was added SnCl2 (2.37 g, 10.5 mmol). The reaction mixture was stirred at 80° C. for 1.5 hours before cooling to cool to RT. The resultant mixture was partitioned between ethyl acetate and water and the phases separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (NaSO4), filtered, and the solvent removed in vacuo. The resulting residue was subjected to flash chromatography (SiO2, gradient 40-50% ethyl acetate in cyclohexane) to give the title compound as a yellow solid (752 mg, 91%). LCMS (Method G): RT=3.35 min, [M+H]+=394.

후처리

  1. temperaturebefore cooling
  2. temperatureto cool to RT
  3. customThe resultant mixture was partitioned between ethyl acetate and water
  4. customthe phases separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (NaSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-6deb19dd29004bb4bf3de08ea5d9c326
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

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