Hydrochloric Acid → HCID 19700860, compound

HRID 861961Notes

Reaction equation

HRID 861961 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH:22]([CH3:24])[CH3:23].Cl>O1CCCC1>[CH3:23][CH:22]([N:10]1[C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:9]1)[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 19700680HCID 19700680, compound

Product 1

HCID 19700860HCID 19700860, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 8- (3-chlorophenyl)pyrido [2,3 -d]pyridazin-5-one (0.33 g, 1.28 mmoles) in tetrahydrofuran (50 ml) was added sodium hydride (0.07 g, 1.53 mmoles). The mixture was stirred at room temperature for 30 minutes under an inert atmosphere. 2-Iodopropane (0.64 ml, 6.4 mmoles) was added and the mixture refluxed for 48 hours. The mixture was cooled and acidified by the addition of 50 ml of 1N HCl. The mixture was extracted with ethyl acetate (3×50 ml) and dried over magnesium sulfate. The solution was filtered and the solvent removed to yield the crude product. The product was purified by crystallization (ethyl ether/hexane) yielding 0.15 g of 6-(2-propyl)-8-(3-chlorophenyl)pyrido[2,3-d]pyridazin-5-one (39%), mp 80°-81° C.

Workup

  1. temperaturethe mixture refluxed for 48 hours
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed
  7. customto yield the crude product
  8. customThe product was purified by crystallization (ethyl ether/hexane)

Sources & evidence

ORD record
ord-2a71540d701c4ff287b8507b8190dced
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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