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Ethanol → 4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]ethoxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde oxime

HRID 346986
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HRID 346986 반응식
Cl.[NH2:2][OH:3].Cl.[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([OH:37])([C:31]4[N:35]([CH3:36])[CH:34]=[N:33][CH:32]=4)[C:23]4[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=4)[CH:20]=3)[NH:15][C:14](=[O:38])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1.C([O-])([O-])=O.[K+].[K+].[CH2:45](O)[CH3:46]>>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:37][CH2:45][CH3:46])([C:31]4[N:35]([CH3:36])[CH:34]=[N:33][CH:32]=4)[C:23]4[CH:30]=[CH:29][C:26]([CH:27]=[N:2][OH:3])=[CH:25][CH:24]=4)[CH:20]=3)[NH:15][C:14](=[O:38])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1
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참가 물질

5

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 21082104(+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde monohydrochloride

생성물 1

HCID 867603784-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]ethoxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde oxime

실험 절차

Hydroxylamine, hydrochloride (0.0131 mol) was added to a solution of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde monohydrochloride (described in Example B1) (0.0087 mol) in ethanol (45 ml). The mixture was stirred at room temperature for 1 hour and 30 minutes then refluxed for 2 hours, poured out into K2CO3 10% and extracted with EtOAc. The organic layer was separated, dried MgSO4), filtered and the solvent was evaporated. The residue (4.86 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding: two fractions. The first fraction was crystallized from CH3CN/diethyl ether. The precipitate was filtered off and dried, yielding 1.69 g (38%) of -4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]ethoxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde oxime, of indeterminate E/Z configuration mp. 232° C. The second fraction was crystallized from CH3CN/diethyl ether. The precipitate was filtered off and dried, yielding 1.91 g (45%) of -4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde oxime, of indeterminate E/Z configuration, mp. 230° C.

후처리

  1. temperaturethen refluxed for 2 hours
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. filtrationdried MgSO4), filtered
  5. customthe solvent was evaporated
  6. customThe residue (4.86 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customyielding
  10. customThe first fraction was crystallized from CH3CN/diethyl ether
  11. filtrationThe precipitate was filtered off
  12. customdried

출처 및 근거

ORD 기록
ord-9f508ccf373141a3b814f1e753c4496a
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07173040B2

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