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Sodium hydride → Ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylate

HRID 2073832
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HRID 2073832 반응식
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[NH:4][CH:5]=[C:6]([C:12](=[O:24])[C:13]1[C:18]([CH3:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1F)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+]>C1COCC1>[F:20][C:17]1[C:18]([CH3:19])=[C:13]2[C:14](=[C:15]([F:22])[C:16]=1[F:21])[N:4]([C:3]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=1[F:1])[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]2=[O:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 178471929HCID 178471929, 화합물

생성물 1

HCID 14651271Ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylate수율 58.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cold (5° C.) solution of 2.77 g (6.64 mmol) of ethyl 3-(2,4-difluoroanilino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)acrylate in 60 ml of dry THF was added 0.32 g of 60% sodium hydride. The solution was stirred overnight at room temperature, then concentrated to an orange foam. The residue was partitioned between methylene chloride and 1N HCl. The organic phase was washed with water, dried over magnesium sulfate, and concentrated to an orange solid which was recrystallized (ethyl acetate:hexane) to give 1.55 g of the title compound, mp 152°-154° C.

후처리

  1. concentrationconcentrated to an orange foam
  2. customThe residue was partitioned between methylene chloride and 1N HCl
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to an orange solid which
  6. customwas recrystallized (ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-14d46361b3284f35a2b109ccccd2f23d
출처 데이터셋
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04920120

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