Ethanol → Ethyl 3-hydroxypyridazine-4-carboxylate

HRID 2076824ノート

反応式

HRID 2076824 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

HCID 12376255Ethyl 3-hydroxypyridazine-4-carboxylate収率 31%

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-cb10b7502a064d748c99d6f808eb1538
出典データセット
uspto-grants-2011_04
特許番号
US07928106B2

反応ノート

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