Hydrochloric Acid → Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 14359

反応式

HRID 14359 の反応式
C([C:3](CC)([C:7]([O-:9])=[O:8])C([O-])=O)C.[H-].[Na+].[H][H].[C:16]12[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:21][C:20](=[O:27])[O:19][C:17]2=O.Cl.[CH3:29][C:30](N(C)C)=O>>[CH2:29]([O:9][C:7]([C:3]1[C:20](=[O:27])[NH:21][C:22]2[C:16]([C:17]=1[OH:19])=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:8])[CH3:30]

参加物

7

反応物 6

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 31374Dimethylacetamide2 回HCID 69515632,2-DiethylpropanedioateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 54684458Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate収率 47%

反応条件

温度
90 °C

実験手順

A solution of diethylmalonate (80 g, 0.50 mol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 22 g, 0.55 mol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and cooled to room temperature. A solution of isatoic anhydride (89.72 g, 0.55 mmol) in dimethylacetamide was added slowly and heated at 120° C. for 15 h. The mixture was cooled to room temperature, poured into ice water and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 55 g (47%) of white solids. Mp 173° C. 1H NMR (DMSO-d6): δ 1.30 (t, J=6.9 Hz, 3H), 4.33 (q, J=6.9 Hz, 2H), 7.18 (t, J=7.5 Hz, 1H), 7.26 (d, J=8.2 Hz, 1H), 7.62 (t, J=7.2 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H) 11.50 (s, 1H), 13.5 (s, 1H). EIMS m/z 234 (M+1), 256 (M+23). Anal. (C12H11NO4) C, H, N.

後処理

  1. temperaturecooled to room temperature
  2. temperatureheated at 120° C. for 15 h
  3. temperatureThe mixture was cooled to room temperature
  4. customThe solids formed
  5. filtrationwere filtered
  6. washwashed several times by water

出典と根拠

ORDレコード
ord-a1cdaf3f18bd4fe08726851b5c339e82
出典データセット
uspto-grants-2010_06
特許番号
US07732146B2

関連ノート

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