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

HRID 14359

반응식

HRID 14359 반응식
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]

참가 물질

7

반응물 6

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 31374Dimethylacetamide2회HCID 69515632,2-DiethylpropanedioateHCID 178418361HCID 178418361, 화합물

생성물 1

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

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a1cdaf3f18bd4fe08726851b5c339e82
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732146B2

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