Ethanol → Ethyl 3-hydroxypyridazine-4-carboxylate

HRID 2076824Notes

Reaction equation

HRID 2076824 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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+].

Workup

  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)

Sources & evidence

ORD record
ord-cb10b7502a064d748c99d6f808eb1538
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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