Ethyl oxoacetate → Acetic acid, [(6-chloro-3-pyridazinyl)hydrazono]-, ethyl ester

HRID 521574Notes

Reaction equation

HRID 521574 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:8][NH2:9])=[CH:6][CH:7]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=O>CO>[CH2:15]([O:14][C:10]([CH:11]=[N:9][NH:8][C:5]1[N:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 70211Ethyl oxoacetateHCID 1007873-Chloro-6-hydrazinopyridazine

Product 1

HCID 71367215Acetic acid, [(6-chloro-3-pyridazinyl)hydrazono]-, ethyl esterYield 68.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound 3-chloro-6-hydrazinylpyridazine (8.85 g, 0.061 mol) and ethyl glyoxalate (6.16 g, 0.061 mol) in 50 mL of methanol containing about 30% acetic acid was stirred at room temperature for 2 h. The yielded solid was collected by filtration and washed with methanol to give product 1-ethoxycarbonylmethylene-2-(6-chloro-3-pyridazinyl) hydrazine as a white solid (9.5 g, 68%). LRMS (M+H+) m/z: calcd 229.03; found 229. 1H NMR (300 MHz, CDCl3): δ 12.40 (s, 1H), 7.80-7.31 (d, J=9.6 Hz, 1H), 7.60-7.56 (d, J=9.3 Hz, 1H), 7.50 (s, 1H), 4.25-4.23 (q, 2H), 1.31-1.26 (t, 3H).

Workup

  1. filtrationThe yielded solid was collected by filtration
  2. washwashed with methanol

Sources & evidence

ORD record
ord-fbcb84034ff341f2af339d49a9edcf4a
Source dataset
uspto-grants-2016_05
Patent number
US09328117B2

Reaction notes

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