p-Toluenesulfonic acid monohydrate → HCID 19006957, compound

HRID 1742586Notes

Reaction equation

HRID 1742586 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl[C:30]1[N:35]=[N:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[C:14]([NH:13][C:11]1[CH:10]=[CH:9][C:3]2[C:4](=[O:6])[N:35]3[N:34]=[C:33]([C:36]([O:38][CH3:39])=[O:37])[CH:32]=[CH:31][C:30]3=[N:1][C:2]=2[CH:12]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12379801Methyl 6-chloropyridazine-3-carboxylateHCID 19006952HCID 19006952, compound

Product 1

HCID 19006957HCID 19006957, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 2-amino-4-(acetylamino)benzoate (4.03 g, 18.13 mmol, Example 4, Step A), p-toluenesulfonic acid, monohydrate (0.5 g, 2.63 mmol) and methyl 6-chloro-3-pyridazinecarboxylate [3.13 g, 18.14 mmol, prepared according to the procedure of Barlin, G. B. and Yap, C. Y. (Aust. J. Chem. 1977, 30, 2319-2322)] in 500 mL of toluene was refluxed under Dean-Stark conditions for 12 h. The mixture was concentrated, dissolved into chloroform, washed with saturated sodium bicarbonate solution, dried (MgSO4), filtered and concentrated. Medium pressure chromatography (silica gel, 5% methanol in chloroform) afforded methyl 7-acetylamino-10-oxo-10H-pyridazino[6,1-b]-quinazoline-2-carboxylate as a yellow solid, mp 281°-285° C., dec.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved into chloroform
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b610c9d4aa4149b8bb7cd27951d734f1
Source dataset
uspto-grants-1994_08
Patent number
US05340808

Reaction notes

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