Hydrochloric Acid → 5-chloro-7-methoxy-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione

HRID 735261노트

반응식

HRID 735261 반응식
CO[C:3](=[O:25])[C:4]1[C:9]([Cl:10])=[CH:8][C:7](Cl)=[CH:6][C:5]=1[NH:12][C:13](=[O:24])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH3:15].[H-].[Na+].Cl.C1C[O:32][CH2:31]C1>>[Cl:10][C:9]1[CH:8]=[C:7]([O:32][CH3:31])[CH:6]=[C:5]2[C:4]=1[C:3](=[O:25])[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([CH3:15])[C:13](=[O:24])[NH:12]2

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 688184034,6-Dichloro-2-[2-(4-methoxy-phenyl)-propionylamino]-benzoic acid methyl ester

생성물 1

HCID 115447385-chloro-7-methoxy-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione수율 41%

실험 절차

To a solution of 4,6-dichloro-2-[2-(4-methoxy-phenyl)-propionylamino]-benzoic acid methyl ester (1.00 g, 2.62 mmol) in dry THF (30 mL) was added NaH (0.32 g, 7.86 mmol, 60% dispersed in mineral oil) at room temperature. The reaction mixture was stirred for 10 hours at reflux temperature, and then poured into 1N HCl aqueous solution. The resulting mixture was extracted with ethyl acetate (100 mL×2). The organic layer was washed with brine (100 mL) and water (100 mL×2), dried over anhydrous MgSO4, and concentrated in vacuo. The objective compound (0.36 g, 41%) was obtained as pale yellow solid by a flash column chromatography (n-hexane:EtOAc=2:1): 1H NMR (200 MHz, CDCl3) δ 1.71 (s, 3H, CH3), 3.71 (s, 3H, OCH3), 3.89 (s, 3H, OCH3), 6.46 (d, J=1.6 Hz, 1H, ArH) 6.56 (d, J=1.6 Hz, 1H, ArH), 6.77 (dd, J=6.9 Hz, 2.0 Hz, 2H, ArH), 7.14 (dd, J=6.9 Hz, 2.0 Hz, 2H, ArH), 8.77 (br s, 1H, NH); m.p. 222-224° C.; MS(EI) m/e 345 [M+], 162, 134, 119, 91; HRMS m/e cacld. for C18H16NO4Cl 345.0768, found 345.0759.

후처리

  1. temperatureat reflux temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×2)
  3. washThe organic layer was washed with brine (100 mL) and water (100 mL×2)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d0e90da2ca594b98a5953e6ee35b4946
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592457B2

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