Methyl 2-chloro-3-oxopentanoate → HCID 22024701, compound

HRID 500994Notes

Reaction equation

HRID 500994 reaction equation
Cl[CH:2]([C:7](=O)[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[C:19]1[CH:24]=[CH:23][N:22]=[N:21][C:20]=1[NH2:25]>O>[CH3:6][O:5][C:3]([C:2]1[N:21]2[N:22]=[CH:23][CH:24]=[C:19]([C:13]3[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=3[CH3:11])[C:20]2=[N:25][C:7]=1[CH2:8][CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 545096Methyl 2-chloro-3-oxopentanoateHCID 22024458HCID 22024458, compound

Product 1

HCID 22024701HCID 22024701, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

Methyl 2-chloro-3-oxopentanoate (5 mL) was added to 4-(2,4-dimethylphenyl)-3-pyridazineamine (640 mg, 3.2 mmol), and the mixture was heated at 155° C. for 30 minutes. Water was added to the resulting reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a 5N aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:N-hexane=1:3) to give the title compound (373 mg, 37%) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a 5N aqueous sodium hydroxide solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:N-hexane=1:3)

Sources & evidence

ORD record
ord-ddc5803a7ecb4c3c907be3b877a23c68
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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