p-Toluenesulfonic acid → HCID 22267315, compound

HRID 488724Notes

Reaction equation

HRID 488724 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6](Cl)[C:5]2=[CH:9][CH:10]=[CH:11][N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[C:4]2=[N:3]1.[C:21]1([CH3:31])[CH:26]=CC(S(O)(=O)=O)=CC=1>C(NCCC)CC>[CH3:1][N:2]1[CH:7]=[C:6]([N:2]([CH2:26][CH2:21][CH3:31])[CH2:7][CH2:6][CH3:5])[C:5]2=[CH:9][CH:10]=[CH:11][N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[C:4]2=[N:3]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22267305HCID 22267305, compound

Product 1

HCID 22267315HCID 22267315, compound

Reagents, catalysts & solvents 1

HCID 8902DipropylamineSolvent

Procedure

Heat a mixture of 2-methyl-4-chloro-8-(3,4-dichlorophenyl)pyrido[2,3-c]pyridazine (4) (1.0 g, 3.1 mmol) and p-toluenesulfonic acid (1.6 g) in 5 mL of di-n-propylamine in a sealed tube at 180° C. for 48 hours. Cool the reaction mixture to ambient temperature and partition between ethyl acetate and water. Wash the organic layer with water and dry over MgSO4. Evaporate the dried solution and purify the desired product 5 by flash chromatography.

Workup

  1. temperatureHeat
  2. custompartition between ethyl acetate and water
  3. washWash the organic layer with water
  4. dry with materialdry over MgSO4
  5. customEvaporate the dried solution
  6. custompurify the desired product 5 by flash chromatography

Sources & evidence

ORD record
ord-679d5e9abcaa441a851417b96a9bab86
Source dataset
uspto-grants-2005_12
Patent number
US06974808B2

Reaction notes

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