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4-(Benzyloxy)-2-methylaniline → 1-(2-Methyl-4-benzyloxyphenyl)-4-[(2-hydroxyethyl)amino]-6-beta,beta,beta-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 849216
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HRID 849216 반응식
O=[C:2]1[C:11]2[CH2:12][CH2:13]O[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:4]=2[NH:3]1.[CH2:21]([O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[C:31]([CH3:36])[CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)COCCO.O>[CH3:36][C:31]1[CH:30]=[C:29]([O:28][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:35]=[CH:34][C:32]=1[N:33]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:4]=3[N:3]=[C:2]([NH:3][CH2:4][CH2:5][OH:15])[C:11]=2[CH2:12][CH2:13]1
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참가 물질

5

반응물 2

HCID 167730534-(Benzyloxy)-2-methylanilineHCID 193698434-Oxo-6-beta,beta,beta-trifluoroethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline

생성물 1

HCID 193698341-(2-Methyl-4-benzyloxyphenyl)-4-[(2-hydroxyethyl)amino]-6-beta,beta,beta-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline수율 86%

시약·촉매·용매 2

HCID 962Water용매
HCID 8117
Diethylene Glycol
용매

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온도
250 °C

실험 절차

4-Oxo-6-β,β,β-trifluoroethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline(5.7 g, 20.0 mmol) was dissolved in diethylene glycol(70 ml) and crude 4-benzyloxy-2-methyl aniline(5.6 g, 26.0 mmol) was added. The reaction mixture was refluxed at 250° C. for 15 hours. The reaction mixture was dissolved in water, extracted with dichloromethane, and the organic layer was washed with water for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography(ethyl acetate:dichloromethane=1:1) to obtain 4.5 g of desired compound as solid in 47% of yield.

후처리

  1. extractionextracted with dichloromethane
  2. washthe organic layer was washed with water for 3 times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography(ethyl acetate:dichloromethane=1:1)

출처 및 근거

ORD 기록
ord-eac70824543a4d88831844bc2ef6e005
출처 데이터셋
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06011044

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