Phosphorus pentachloride → HCID 13526620, compound

HRID 986749Notes

Reaction equation

HRID 986749 reaction equation
[C:1]1([C:7]2[N:20]=[N:19][C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:11](=O)[NH:10][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:23]>P(Cl)(Cl)(Cl)=O>[Cl:23][C:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[C:18]2[N:19]=[N:20][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 13526616HCID 13526616, compound

Product 1

HCID 13526620HCID 13526620, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Phosphorus oxychloride (760 ml), 3-phenyl-pyridazino[4,3-c]isoquinolin-6(5H)-one (74 g, 0.27 mol) and phosphorus pentachloride (58 g, 0.278 mol) in a 2 litre flask are heated to reflux temperature with stirring. Heating is continued for about 3.5 hours, then a solution is obtained which is evaporated under reduced pressure to eliminate the phosphorus oxychloride excess. The solid is taken up with benzene and then evaporated to dryness in order to eliminate all the unreacted phosphorus oxychloride. Then the reaction mass is taken up with methylene chloride (1500 ml) and washed with 10% aqueous ammonium acetate (two times; first with 800 ml and then with 400 ml), and subsequently with water up to neutrality. The methylene chloride phase is dried on magnesium sulfate and the solvent is evaporated under reduced pressure. The solid residue is disaggregated and washed with methylene chloride (300 ml) and filtered, yielding 6-chloro-3-phenyl-pyridazino-[4,3-c]isoquinoline (63 g). By concentrating the mother liquors to dryness and crystallizing the obtained solid from acetone, 11 g of the same product is obtained. These two crops of 6-chloro 3-phenylpyridazino[4,3-c]isoquinoline derivatives are pooled and recrystallized from acetone, with a 90% overall yield. The product has a melting point of 177°-178° C.

Workup

  1. temperatureto reflux temperature
  2. temperatureHeating
  3. customa solution is obtained which
  4. customis evaporated under reduced pressure
  5. customevaporated to dryness in order
  6. washwashed with 10% aqueous ammonium acetate (two times
  7. dry with materialThe methylene chloride phase is dried on magnesium sulfate
  8. customthe solvent is evaporated under reduced pressure
  9. washwashed with methylene chloride (300 ml)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-5dbe6bd986444e76b2fbb76366c91502
Source dataset
uspto-grants-1987_12
Patent number
US04716159

Reaction notes

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