Hydrochloric Acid → 3-Chloro-6-(3-methoxy-4-propoxyphenyl)pyridazine

HRID 2254558Notes

Reaction equation

HRID 2254558 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[CH:15][C:16](=O)[NH:17][N:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH3:12].[ClH:20]>O=P(Cl)(Cl)Cl>[Cl:20][C:16]1[N:17]=[N:18][C:13]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10220820HCID 10220820, compound

Product 1

HCID 193854943-Chloro-6-(3-methoxy-4-propoxyphenyl)pyridazineYield 98.8%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
100 °C

Procedure

18.0 g 6-(3-methoxy-4-n-propoxyphenyl)-3[2H]pyridazinone are suspended in 63.6 g phosphorus oxytrichloride. The mixture is stirred at 100° C. until a clear solution has formed and the evolution of HCl stops. The solution is cooled to about 50° C. and poured onto 1 kg of ice, while stirring constantly, whereupon a crystalline precipitate forms immediately, this being filtered off with suction and washed free from acid with water, dilute sodium bicarbonate solution and again with water. Drying in vacuo gives 19.1 g (98.8%) of the title compound of m.p. 129° C., and of m.p. 132° C. after crystallization from cyclohexane.

Workup

  1. customhas formed
  2. temperatureThe solution is cooled to about 50° C.
  3. stirringwhile stirring constantly, whereupon a crystalline precipitate forms immediately
  4. filtrationthis being filtered off with suction
  5. washwashed free from acid with water, dilute sodium bicarbonate solution and again with water
  6. customDrying in vacuo

Sources & evidence

ORD record
ord-373b9817fe304e79a8fc37e63cc1d004
Source dataset
uspto-grants-1993_08
Patent number
US05236918

Reaction notes

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