Sodium ethoxide → HCID 66663076, compound

HRID 1685065Notes

Reaction equation

HRID 1685065 reaction equation
[CH3:1][C:2]12[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]1([CH3:13])[CH2:5][N:4]=[N:3]2.CC[O-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([CH3:13])=[CH:5][NH:4][N:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 58055077HCID 58055077, compound

Product 1

HCID 66663076HCID 66663076, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 1,5-dimethyl-2,3-diaza-bicyclo[3.1.0]hex-2-ene-6-carboxylate (1.25 g, 6.9 mmol) in ethanol (20 mL) was added a solution of NaOEt in ethanol (7 mL 0.2N) and the mixture was stirred for 10 min The resulting solution was partitioned between diethyl ether and water. The organic phase was isolated and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried over MgSO4 and the volatiles were removed in vacuo to afford ethyl 3,5-dimethyl-1,4-dihydropyridazine-4-carboxylate (1.0 g, 5.5 mmol, 80%) which was partially (circa 50%) oxidized to the pyridazine analog.

Workup

  1. customwas partitioned between diethyl ether and water
  2. customThe organic phase was isolated
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-12f63667c9294a908a0f6e86a6b08fca
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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