Hydrochloric Acid → 7-Chloro-4-hydroxy-2-(3,4-dimethoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione

HRID 1600051노트

반응식

HRID 1600051 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:15]([O:17]C)=O)=[C:8]([C:12](Cl)=[O:13])[NH:9]2)=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([NH:30][NH2:31])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:19])[C:7]3[C:15](=[O:17])[N:30]([C:24]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=4)[N:31]=[C:12]([OH:13])[C:8]=3[NH:9][C:10]=2[CH:11]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 88491(3,4-Dimethoxyphenyl)hydrazineHCID 219976803-Carbomethoxy-7-chloro-4-hydroxyquinoline-2-carbonyl chloride

생성물 1

HCID 1784920847-Chloro-4-hydroxy-2-(3,4-dimethoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione수율 10.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

7-Chloro-3-methoxycarbonyl-4-oxo-1,4-dihydroquinoline-2-carbonyl chloride (7.00 g, 23.3 mM) was dissolved in tetrahydrofuran (210 mL) and added dropwise over 20 minutes to a cold (0° C.) solution of 3,4-dimethoxyphenylhydrazine (9.80 g, 58.3 mM) in tetrahydrofuran (420 mL)with stirring. The resulting brown suspension was stirred at 0° C. for 30 minutes and at room temperature for 2 hours. Ice/water slurry (450 mL) was added to the reaction mixture followed by 1N HCl (1.2 L) and the brown suspension was stirred for 1 hour. The solids were separated by filtration and washed with water and then ether to provide7-chloro-3-methoxycarbonyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid N-2-(2,4-dimethoxyphenyl)hydrazide (15 g, wet). The combined filtrateand washes were partially concentrated to remove the THF whereupon a precipitate formed. This precipitate was collected and washed with water and then ether to give the crude title compound (2.00 g). Recrystallization of this crude from refluxing methanol (500 mL) gave the title compound (0.98 g, 10%) as a tan powder, mp=334°-336° C.; HS(CI): 400 (M+H).

후처리

  1. stirringThe resulting brown suspension was stirred at 0° C. for 30 minutes and at room temperature for 2 hours
  2. stirringthe brown suspension was stirred for 1 hour
  3. customThe solids were separated by filtration
  4. washwashed with water
  5. concentrationThe combined filtrateand washes were partially concentrated
  6. customto remove the THF whereupon a precipitate
  7. customformed
  8. customThis precipitate was collected
  9. washwashed with water
  10. customether to give the crude title compound (2.00 g)
  11. customRecrystallization of this crude
  12. temperaturefrom refluxing methanol (500 mL)

출처 및 근거

ORD 기록
ord-657dea9b8ce742fca0fe7e5df0830b13
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744471

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