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

HRID 1924238Notes

Reaction equation

HRID 1924238 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-9e3fc2e8ff2b41a58ecf1a6a286f9c03
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

Loading…