Hydrochloric Acid → HCID 86600906, compound

HRID 915013Notes

Reaction equation

HRID 915013 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:13])[N:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1)(=[O:3])[CH3:2].C([O:18][N:19]=O)(C)(C)C.CC(C)([O-])C.Cl>C1COCC1.CCOC(C)=O.O>[CH:10]([N:8]1[C:7](=[O:13])[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[N:19][OH:18])=[N:9]1)([CH3:11])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 45749132-Methylpropan-2-olateHCID 69331932HCID 69331932, compound

Product 1

HCID 86600906HCID 86600906, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-acetyl-2-isopropyl-3(2H)-pyridazinone (74.0 g) and t-butylnitrite (73.3 ml) in THF (740 ml) was stirred at 0° C. Pottasium t-butoxide (55.3 g) was added to the reaction mixture. Then the reaction mixture was stirred at 25° C. for 1 hour. Water, 1N HCl and EtOAc were added to the reaction mixture. The organic layer was washed with 1N HCl, aq. NaHCO3 and brine. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain (1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)(oxo)-acetaldehyde oxime (15.0 g) as white powder.

Workup

  1. stirringThen the reaction mixture was stirred at 25° C. for 1 hour
  2. washThe organic layer was washed with 1N HCl, aq. NaHCO3 and brine
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with a mixture of n-hexane and EtOAc
  8. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-88427eb741524264aa61ecf46cd7753a
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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