p-Toluenesulfonic acid → HCID 18315617, compound

HRID 275695Notes

Reaction equation

HRID 275695 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](Cl)[C:5]2[C:6]([N:19]=1)=[C:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[N:8]=[N:9][CH:10]=2.[C:21]1([CH3:31])[CH:26]=CC(S(O)(=O)=O)=CC=1>C(NCCC)CC>[CH3:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:26][CH2:21][CH3:31])[CH2:7][CH2:6][CH3:5])[C:5]2[C:6]([N:19]=1)=[C:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[N:8]=[N:9][CH:10]=2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22267310HCID 22267310, compound

Product 1

HCID 18315617HCID 18315617, compound

Reagents, catalysts & solvents 1

HCID 8902DipropylamineSolvent

Procedure

Heat a mixture of 2-methyl-4-chloro-8-(3,4-dichlorophenyl)pyrido[2,3-d]pyridazine (4) (2.0 g, 6.2 mmol) and p-toluenesulfonic acid (3.2 g) in 10 mL of di-n-propylamine in a sealed tube at 180° C. for 48 hours. Cool the reaction mixture to ambient temperature and partition the reaction mixture between ethyl acetate and water. Wash the organic layer with water and dry over MgSO4. Evaporate the dried solution and purify the product 5 by flash chromatography.

Workup

  1. temperatureHeat
  2. custompartition the reaction mixture 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 product 5 by flash chromatography

Sources & evidence

ORD record
ord-bf4364018ba4401dbebf9b72428fccc0
Source dataset
uspto-grants-2002_03
Patent number
US06352990B1

Reaction notes

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