4-Chloroaniline → N-(4-chlorophenyl)-4,5-dimethyl-6-(pyridin-4-ylmethyl)pyridazin-3-amine

HRID 49914Notes

Reaction equation

HRID 49914 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:6]([CH3:9])[C:7]=1[CH3:8].[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[N:3]=[N:4][C:5]([CH2:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]([CH3:9])[C:7]=2[CH3:8])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 107760253-Chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

Product 1

HCID 6419385N-(4-chlorophenyl)-4,5-dimethyl-6-(pyridin-4-ylmethyl)pyridazin-3-amine

Procedure

A solution of 0.070 g 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine and 0.153 g para-chloroaniline is heated in a sealed tube for 20 h to 130° C. After cooling to RT, the solution is concentrated by evaporation, the residue diluted with 100 ml CH2Cl2 and then extracted with 100 ml sat. aqueous NaHCO3 solution. The organic phase is dried over MgSO4, concentrated by evaporation, and the residue purified by flash chromatography (FC) on silica gel in Ch2Cl2/methanol 19/1. The title compound is obtained: m.p. 196-199° C. 1H-NMR (250 MHz, CDCl3): δ=8.45 (s, wide, 2H); 7.55 (d, 2H); 7.25 (d, 2H); 7.10 (d, 2H); 6.20 (s, wide, 1H); 4.25 (s, 2H); 2.15 (s, 3H); 2.10 (s, 3H). ES-MS 325, 327 (M+H for 35Cl and 37Cl).

Workup

  1. concentrationthe solution is concentrated by evaporation
  2. additionthe residue diluted with 100 ml CH2Cl2
  3. extractionextracted with 100 ml sat. aqueous NaHCO3 solution
  4. dry with materialThe organic phase is dried over MgSO4
  5. concentrationconcentrated by evaporation
  6. customthe residue purified by flash chromatography (FC) on silica gel in Ch2Cl2/methanol 19/1

Sources & evidence

ORD record
ord-bfcdf60b8c78469f82abe1bcb2c33ccd
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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