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

HRID 735261ノート

反応式

HRID 735261 の反応式
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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d0e90da2ca594b98a5953e6ee35b4946
出典データセット
uspto-grants-2009_09
特許番号
US07592457B2

反応ノート

読み込み中…