Ethyl formate → Racemic Ethyl 6,7-Dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

HRID 597198노트

반응식

HRID 597198 반응식
[O-:1][CH2:2]C.[Na+].[H-].[Na+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]([CH3:26])[CH2:13][C:12]2=[O:27].C(OCC)=O>C1C=CC=CC=1.C(O)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]([CH3:26])[C:13](=[CH:2][OH:1])[C:12]2=[O:27]

참가 물질

7

반응물 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 15480676ethyl 6,7-dimethoxy-2-methyl-4-oxo-3,4-dihydro-1(2H)-quinolinecarboxylate

생성물 1

HCID 70638946Racemic Ethyl 6,7-Dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate수율 96%

시약·촉매·용매 2

HCID 241Benzene용매HCID 702Ethanol용매

실험 절차

To sodium ethoxide, freshly prepared from 4.8 g. of sodium hydride and 6.0 ml. of ethanol was added a solution of 14.7 g. of ethyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate and 19.8 ml. of ethyl formate in 150 ml. of benzene, over a 45 min. period. The reaction mixture was stirred at room temperature for 3 hrs. and then it was poured onto 250 ml. of ice water. The layers were separated, and the organic layer was extracted with 1N sodium hydroxide solution. The combined aqueous phases were washed with benzene, and then they were added dropwise to 250 ml. of 12N hydrochloric acid. This caused the product to separate in the form of an oil. Recrystallization of this oil from hexane produced 15.4 g. (96% yield) of the title compound, m.p. 98°-101° C. Further recrystallization from hexane raised the melting point to 129°-130° C.

후처리

  1. additionand then it was poured onto 250 ml
  2. customThe layers were separated
  3. extractionthe organic layer was extracted with 1N sodium hydroxide solution
  4. washThe combined aqueous phases were washed with benzene
  5. additionthey were added dropwise to 250 ml
  6. customto separate in the form of an oil
  7. customRecrystallization of this oil from hexane
  8. customproduced 15.4 g

출처 및 근거

ORD 기록
ord-14c804e5e53a421a9bade78cbb7dd5c2
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04013662

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