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Diisopropylethylamine → [4-(3-Fluoro-4-nitrophenoxy)-7-methoxyquinolin-6-yl]carbamic acid benzyl ester

HRID 853389
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HRID 853389 반응식
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][C:26]1[CH:27]=[C:28]([OH:35])[CH:29]=[CH:30][C:31]=1[N+:32]([O-:34])=[O:33].C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:35][C:28]1[CH:29]=[CH:30][C:31]([N+:32]([O-:34])=[O:33])=[C:26]([F:25])[CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5209483-Fluoro-4-nitrophenolHCID 58931435(4-Chloro-7-methoxyquinolin-6-yl)carbamic acid benzyl ester

생성물 1

HCID 58931261[4-(3-Fluoro-4-nitrophenoxy)-7-methoxyquinolin-6-yl]carbamic acid benzyl ester수율 8.8%

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
130 °C

실험 절차

(4-Chloro-7-methoxyquinolin-6-yl)carbamic acid benzyl ester (1.58 g) was added to 1-methyl-2-pyrrolidone (5 ml), and then 3-fluoro-4-nitrophenol (0.87 g) and N,N-diisopropylethylamine (1.2 ml) were added and the mixture was heated and stirred at 130° C. for 6 hours. The reaction solution was poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over magnesium sulfate. The organic layer was concentrated and the obtained residue was subjected to NH silica gel column chromatography for elution with a solvent (ethyl acetate) to obtain the title compound (188 mg) as a solid.

후처리

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe organic layer was concentrated
  6. washthe obtained residue was subjected to NH silica gel column chromatography for elution with a solvent (ethyl acetate)

출처 및 근거

ORD 기록
ord-88878d7c8be8428e862b67100cf2403d
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253286B2

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