Ethanol → HCID 53856373, compound

HRID 2419019Notes

Reaction equation

HRID 2419019 reaction equation
[C:1]([C:3]1[N:4]=[N:5][C:6]([N:9]([CH3:11])[CH3:10])=[CH:7][CH:8]=1)#N.[OH2:12].[OH-].[Na+].[CH2:15]([OH:17])[CH3:16]>C(Cl)Cl>[CH3:11][N:9]([CH3:10])[C:6]1[N:5]=[N:4][C:3]([C:1]([O:17][CH2:15][CH3:16])=[O:12])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 21327996HCID 21327996, compound

Product 1

HCID 53856373HCID 53856373, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl (6-dimethylaminopyridazin-3-yl)carboxylate can be obtained by heating, at a temperature of about 70° C for 4.5 hours, a suspension of 3-cyano-6-dimethylaminopyridazine (52.7 g) in a mixture of distilled water (600 cc), 10N aqueous sodium hydroxide solution (200 cc) and ethanol (400 cc). After cooling to a temperature of about 20° C, methylene chloride (200 cc) is added to the reaction mixture, which is then left to stand for 12 hours at a temperature of about 20° C. The aqueous phase is removed by decantation, acidified by addition of 12N hydrochloric acid (150 cc) and evaporated to dryness under reduced pressure. Ethanol (360 cc), 1,2-dichloroethane (360 cc) and pure methanesulphonic acid (76 g) are added to the residue thus obtained. The resulting mixture is then heated under reflux for 20 hours. After cooling to a temperature of about 20° C, the insoluble matter which has formed is filtered off and washed with methylene chloride (3 × 20 cc). A saturated aqueous sodium carbonate solution (720 cc) is added to the filtrate thus obtained. The insoluble product which forms is filtered off and washed with methylene chloride (2 × 200 cc). The aqueous phase is removed by decantation and is washed with methylene chloride (2 × 100 cc). The combined organic fractions are dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure. Ethyl (6-dimethylaminopyridazin-3-yl)carboxylate (50.81 g), melting at 112° C, is thus obtained.

Workup

  1. additionis added to the reaction mixture, which
  2. waitis then left
  3. customThe aqueous phase is removed by decantation
  4. additionacidified by addition of 12N hydrochloric acid (150 cc)
  5. customevaporated to dryness under reduced pressure
  6. additionEthanol (360 cc), 1,2-dichloroethane (360 cc) and pure methanesulphonic acid (76 g) are added to the residue
  7. customthus obtained
  8. temperatureThe resulting mixture is then heated
  9. temperatureunder reflux for 20 hours
  10. temperatureAfter cooling to a temperature of about 20° C
  11. customthe insoluble matter which has formed
  12. filtrationis filtered off
  13. washwashed with methylene chloride (3 × 20 cc)
  14. additionA saturated aqueous sodium carbonate solution (720 cc) is added to the filtrate
  15. customthus obtained
  16. filtrationThe insoluble product which forms is filtered off
  17. washwashed with methylene chloride (2 × 200 cc)
  18. customThe aqueous phase is removed by decantation
  19. washis washed with methylene chloride (2 × 100 cc)
  20. dry with materialThe combined organic fractions are dried over magnesium sulphate
  21. filtrationfiltered
  22. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-66ecf988f330452bbb83d12b20e39323
Source dataset
uspto-grants-1978_08
Patent number
US04104386

Reaction notes

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