Sodium hydride → HCID 69154689, compound

HRID 2373188Notes

Reaction equation

HRID 2373188 reaction equation
[CH3:1][C:2]1[O:3][N:4]=[C:5]2[C:10]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N:8][NH:7][C:6]2=[O:17].[H-].[Na+].Cl.Cl[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>>[CH3:1][C:2]1[O:3][N:4]=[C:5]2[C:10]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N:8][N:7]([CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[C:6]2=[O:17]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 28482Isoxazole(3,4-d)pyridazin-7(6H)-one, 3-methyl-4-phenyl-HCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 69154689HCID 69154689, compoundYield 79%

Procedure

To a stirred suspension of 3-methyl-4-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one (1.5 g, 6.6 mmol) (Renzi, G.; Pinzauti, S., II Farmaco Ed. Sci. 1969, 24, 885-889), 60% sodium hydride (0.63 g, 15.8 mmol) was added portionwise and the mixture stirred for 15 minutes. Then 4-(chloromethyl)pyridine hydrochloride (1.3 g, 7.9 mmol) was added portionwise and the final mixture was stirred at 50° C. for 7 h, then poured onto water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo to yield a crude product that was crystallized from isopropyl ether/petroleum ether to yield the title compound (1.66 g, 79% yield) as a light brown solid.

Workup

  1. additionwas added portionwise
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto yield a crude product that
  8. customwas crystallized from isopropyl ether/petroleum ether

Sources & evidence

ORD record
ord-dde2ae2f50184c7dbeda3dc6429de608
Source dataset
uspto-grants-2008_12
Patent number
US07459453B2

Reaction notes

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