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

HRID 1057731Notes

Reaction equation

HRID 1057731 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-bbe318d92d72403595b8b3af45b67f55
Source dataset
uspto-grants-2003_02
Patent number
US06514974B2

Reaction notes

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