Ethanol → HCID 53787044, compound

HRID 1390304Notes

Reaction equation

HRID 1390304 reaction equation
[C:1]([C:3]1[N:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#N.[OH2:16].[CH2:17]([OH:19])[CH3:18].[OH-].[Na+]>C(Cl)Cl>[CH3:15][N:12]1[CH2:11][CH2:10][N:9]([C:6]2[N:5]=[N:4][C:3]([C:1]([O:19][CH2:17][CH3:18])=[O:16])=[CH:8][CH:7]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 21329213HCID 21329213, compound

Product 1

HCID 53787044HCID 53787044, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Ethyl [6-(4-methylpiperazin-1-yl)pyridazin-3-yl]-carboxylate can be obtained by heating a suspension of 3-cyano-6-(4-methylpiperazin-1-yl)pyridazine (40.7 g) in a mixture of distilled water (300 cc), ethanol (200 cc) and 10N aqueous sodium hydroxide (100 cc) at a temperature of about 80° C. for 5 hours. After cooling to a temperature of about 20° C., methylene chloride (200 cc) is added to the reaction mixture and the aqueous phase is decanted, acidified with 12N hydrochloric acid (100 cc) and evaporated to dryness under reduced pressure. Ethanol (250 cc), 1,2-dichloroethane (250 cc) and pure methanesulphonic acid (52.5 g) are added to the residue obtained. The resulting mixture is then heated under reflux for 20 hours. After cooling to a temperature of about 20° C., the insoluble material is filtered off and washed with methylene chloride (2 × 100 cc). A saturated aqueous solution of sodium carbonate (1000 cc) is added to the filtrate thus obtained. The resulting insoluble product is filtered off and washed with methylene chloride (2 × 200 cc). The aqueous phase is decanted and washed with methylene chloride (2 × 200 cc). The organic fractions are combined, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure. Ethyl [6-(4-methylpiperazin-1-yl)pyridazin-3-yl]-carboxylate (9.5 g), melting at 106° C., is obtained.

Workup

  1. temperatureby heating
  2. additionis added to the reaction mixture
  3. customthe aqueous phase is decanted
  4. customevaporated to dryness under reduced pressure
  5. additionEthanol (250 cc), 1,2-dichloroethane (250 cc) and pure methanesulphonic acid (52.5 g) are added to the residue
  6. customobtained
  7. temperatureThe resulting mixture is then heated
  8. temperatureunder reflux for 20 hours
  9. filtrationthe insoluble material is filtered off
  10. washwashed with methylene chloride (2 × 100 cc)
  11. additionA saturated aqueous solution of sodium carbonate (1000 cc) is added to the filtrate
  12. customthus obtained
  13. filtrationThe resulting insoluble product is filtered off
  14. washwashed with methylene chloride (2 × 200 cc)
  15. customThe aqueous phase is decanted
  16. washwashed with methylene chloride (2 × 200 cc)
  17. dry with materialdried over magnesium sulphate
  18. filtrationfiltered
  19. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ff5cfbd5068c4b10973265e44ff2b024
Source dataset
uspto-grants-1979_02
Patent number
US04138487

Reaction notes

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