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1,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate) → 5-Fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1873754
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HRID 1873754 반응식
CC1(C)[O:7][C:6](=[O:8])[C:5](=[C:9]([OH:15])[CH:10]=[C:11]([NH:13][CH3:14])[CH3:12])[C:4](=O)[O:3]1.[F:18][B-](F)(F)F.F[B-](F)(F)F.F[N+]1C=CC=CC=1C1C=CC=C[N+]=1F>C(#N)C>[F:18][C:10]1[C:9]([OH:15])=[C:5]([C:6]([OH:7])=[O:8])[C:4](=[O:3])[N:13]([CH3:14])[C:11]=1[CH3:12]
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참가 물질

4

반응물 2

HCID 27339311,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate)HCID 761689572,2-Dimethyl-5-(1-hydroxy-3-methylamino-2-butenylidene)-1,3-dioxane-4,6-dione

생성물 1

HCID 576721225-Fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid수율 108.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

1.0 g of 2,2-dimethyl-5-(1-hydroxy-3-methylamino-2-butenylidene)-1,3-dioxane-4,6-dione was suspended in 20 ml of acetonitrile, 806 mg of N,N′-difluoro-2,2′-bipyridinium bis(tetrafluoroborate) was added thereto, and this was stirred at room temperature for 1 hour and at 50° C. for 30 minutes. The reaction mixture was added to 100 ml of ice water and extracted with 100 ml of chloroform twice. The organic layer was dried with anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel column chromatography (eluent:ethyl acetate) to obtain 480 mg of 5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid represented by the formula:

후처리

  1. extractionextracted with 100 ml of chloroform twice
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af11095f0c5f4ae0a146bc2569e0aad6
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304437B2

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