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

HRID 346643

반응식

HRID 346643 반응식
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].[C:16]12[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:21]C(=O)O[C:17]2=[O:18].Cl>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[NH:21][C:22]2[C:16]([C:17]=1[OH:18])=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:4])[CH3:7]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 54684458Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate수율 33.1%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
90 °C

실험 절차

Neat diethyl malonate (18.05 g, 112.7 mmol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 4.96 mg, 124 mmol) in dimethylacetamide under N2 atmosphere. The mixture was stirred at room temperature until the evolution of hydrogen gas ceased, then the mixture was heated to 90° C. for 30 min. and cooled to room temperature. A solution of isatoic anhydride (20 g, 124 mmol) in dimethylacetamide was added slowly and the mixture heated overnight at 110° C. 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 8.7 g (30%) of white solids. M.P. 173° C. 1H NMR (DMSO-d6): δ 1.31 (t, J=6.6 Hz, 3H), 4.34 (q, J=6.6 Hz, 2H), 7.20 (t, J=8.0 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 7.62 (t, J=7.2 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 11.50 (b, 1H); EIMS: 234 (M+H).

후처리

  1. temperaturecooled to room temperature
  2. temperaturethe mixture heated overnight at 110° C
  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-b8ea3996c6ec4d80ae73da7d15e199b6
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173036B2

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