Acetic Acid → Methyl 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate

HRID 877411Notes

Reaction equation

HRID 877411 reaction equation
O=[C:2]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:3](OC)=[O:4].O.[NH2:14][NH2:15].CC(O)=O>CO.C1(C)C=CC=CC=1>[O:4]=[C:3]1[NH:15][N:14]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 25775Dimethyl alpha-ketoglutarate

Product 1

HCID 12081646Methyl 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Dimethyl 2-oxoglutarate (1.5 g, 8.98 mmol) was dissolved in MeOH (62 mL). Hydrazine monohydrate (500 mg, 9.88 mmol) and AcOH (540 mg, 8.98 mmol) were added to the solution sequentially. The reaction mixture was warmed at 70° C. for 18 h. The solution was cooled and reduced to a residue which was subsequently redissolved in toluene and evaporated to afford an off-white solid. The solid was tritrated with hexanes and needed no further purification (1.2 g, 100%): 1H NMR (CDCl3, 600 MHz) δ 8.75 (s, 1H), 3.90 (s, 3H), 2.93 (t, 2H, J=8.5 Hz), 2.58 (t, 2H, J=8.5 Hz).

Workup

  1. temperatureThe solution was cooled
  2. customevaporated
  3. customto afford an off-white solid
  4. customno further purification (1.2 g, 100%)

Sources & evidence

ORD record
ord-49e4f47e46034af4a7d88308f3ea8212
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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