Isopropanol → 6-Methoxy-7-methylquinoline

HRID 931714

반응식

HRID 931714 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[CH3:12].N[CH2:14][CH2:15][CH2:16]O.C(O)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.O.[Sn](Cl)Cl>O1CCOCC1.O.O.[Ru](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[CH3:12])[N:9]=[CH:16][CH:15]=[CH:14]2

참가 물질

8

반응물 5

HCID 3776IsopropanolHCID 90863-Amino-1-propanolHCID 11776TriphenylphosphineHCID 61436Stannous chloride dihydrateHCID 6435201-Methoxy-2-methyl-4-nitrobenzene

생성물 1

HCID 155348986-Methoxy-7-methylquinoline수율 15.4%

시약·촉매·용매 2

HCID 6093376Ruthenium trichloride hydrate촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
180 °C

실험 절차

1-methoxy-2-methyl-4-nitrobenzene (3A) (5 g, 30.0 mmol), 3-amino-1-propanol (0.57 mL, 7.5 mmol), isopropanol (3.43 mL, 4.5 mmol), ruthenium(III) chloride hydrate (156 mg, 0.75 mmol), triphenylphosphine (588 mg, 2.24 mmol), and tin(II) chloride dihydrate (1.69 g, 7.5 mmol) in dioxane/H2O (67 mL/7 mL) were placed in a stainless steel pressure vessel. After the system was flushed with argon, the mixture was stirred at 180° C. for 20 hours. The reaction mixture was filtered through a short silica gel column (ethyl acetate/chloroform mixture) to eliminate inorganic compounds and concentrated under reduced pressure. The organic layer was poured into saturated brine, extracted with chloroform, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residual oily material was separated by column chromatography to give the product 3B (200 mg, 15%). LCMS-ESI+ (m/z): 174.2 (M+H)+.

후처리

  1. customAfter the system was flushed with argon
  2. filtrationThe reaction mixture was filtered through a short silica gel column (ethyl acetate/chloroform mixture)
  3. concentrationconcentrated under reduced pressure
  4. additionThe organic layer was poured into saturated brine
  5. extractionextracted with chloroform
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residual oily material was separated by column chromatography

출처 및 근거

ORD 기록
ord-777bcf34fd8e427ea76d87be20965b8e
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296758B2

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