Triethylamine → Ethyl 4-[(pyridazin-4-ylmethylene)amino]butanoate

HRID 1896375Notes

Reaction equation

HRID 1896375 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][N:2]=1.Cl.[NH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[N:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 13011721Pyridazine-4-carbaldehyde

Product 1

HCID 57743069Ethyl 4-[(pyridazin-4-ylmethylene)amino]butanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a 25 ml, three-necked flask fitted with a magnetic stirrer under inert atmosphere, pyridazine-4-carbaldehyde x66 (0.93 g, 8.6 mmol) and ethyl 4-aminobutanoate hydrochloride x67 (1.58 g, 9.5 mmol) are dissolved in CHCl3 (15 ml). Triethylamine (1.3 ml, 9.5 mmol) and MgSO4 (2 g) are added and the mixture is stirred at room temperature for 4 h. The mixture is filtered, washed with water, dried over MgSO4 and concentrated to give 1.92 g (100%) of crude ethyl 4-[(pyridazin-4-ylmethylene)amino]butanoate x68, which is used in the next step without further purification.

Workup

  1. filtrationThe mixture is filtered
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c247e8ccd25a49efb0dd455918182522
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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