Hydrochloric Acid → HCID 19700733, compound

HRID 861960Notes

Reaction equation

HRID 861960 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[CH2:22][CH3:23].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:22]([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)[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 19700680HCID 19700680, compound

Product 1

HCID 19700733HCID 19700733, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 8-(3-chlorophenyl)pyrido[2,3-d]pyridazin-5-one (0.32 g, 1.24 mmoles) in tetrahydrofuran (50 ml) was added sodium hydride (0.06 g, 1.4 mmoles). The mixture was stirred for 1 hour at room temperature. Iodoethane (0.48 g, 3.1 mmoles) was added and the solution was refluxed for 18 hours under an inert atmosphere. The mixture was cooled and acidified by the addition of 50 ml of 1N HCl. The desired compound was isolated by extraction with ethyl acetate (extracted until no product detected in aqueous layer), washed with sodium bicarbonate, brine and dried over magnesium sulfate. The solution was filtered and the solvent removed yielding 0.85 g of the crude desired product. The product was purified by recrystallization from methanol to yield 0.24 g of 6-ethyl-8-(3-chlorophenyl)pyrido-[2,3-d]pyridazin-5-one (67.8%), mp. 117°-118° C.

Workup

  1. temperaturethe solution was refluxed for 18 hours under an inert atmosphere
  2. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-0b56611195154a97ae76db6c8ae5be2d
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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