Ethanol → Ethyl 3-hydroxypyridazine-4-carboxylate

HRID 2076824노트

반응식

HRID 2076824 반응식
[O:1]=[C:2]1[C:7]([C:8]#N)=[CH:6][CH:5]=[N:4][NH:3]1.OS(O)(=O)=O.C([O-])([O-])=[O:16].[Na+].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][C:8]([C:7]1[C:2](=[O:1])[NH:3][N:4]=[CH:5][CH:6]=1)=[O:16])[CH3:22]

참가 물질

5

반응물 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 123762563-Oxo-2,3-dihydropyridazine-4-carbonitrile

생성물 1

HCID 12376255Ethyl 3-hydroxypyridazine-4-carboxylate수율 31%

실험 절차

3-Oxo-2,3-dihydro-pyridazine-4-carbonitrile (1 g, 8.26 mmol) was heated in a mixture of ethanol (2 ml) and conc. H2SO4 (1.1 ml) to 100° C. (oil-bath temperature) overnight. The reaction mixture was then allowed to cool to ambient temperature, poured onto ice and carefully neutralized with solid Na2CO3. The mixture was extracted three times with CHCl3 and the combined extracts were dried (Na2SO4) and evaporated. The remaining residue was then purified by column chromatography (silica gel, heptane/ethyl acetate 70:30 to 35:65) to give the title compound (433 mg, 2.58 mmol; 31%) as white solid. MS: m/e=169.1 [M+H+].

후처리

  1. additionpoured onto ice
  2. extractionThe mixture was extracted three times with CHCl3
  3. dry with materialthe combined extracts were dried (Na2SO4)
  4. customevaporated
  5. customThe remaining residue was then purified by column chromatography (silica gel, heptane/ethyl acetate 70:30 to 35:65)

출처 및 근거

ORD 기록
ord-cb10b7502a064d748c99d6f808eb1538
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928106B2

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