Methylhydrazine → HCID 67315552, compound

HRID 1011956Notes

Reaction equation

HRID 1011956 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4](=O)[CH:5]([CH3:18])[C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[CH3:21][NH:22][NH2:23]>>[CH3:1][O:2][C:3]([C:4]1[C:5]([CH3:18])=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[N:22]([CH3:21])[N:23]=1)=[O:20]

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 67314711HCID 67314711, compound

Product 1

HCID 67315552HCID 67315552, compound

Procedure

A solution of 500 mg (2.47 mmol) of trifluoromethylpropiophenone and 0.335 mL (2.47 mmol) of diethyloxalate in 10 mL of MeOH was treated with 133 mg (2.47 mmol) of sodium methylate and stirred at room temperature for 3 hrs. The reaction was quenched by the addition of 10% aqueous KHSO4 and extracted with EtOAc (3×). The organic phases were washed with 10% aqueous KHSO4 and brine, dried over magnesium sulfate and evaporated to give crude 3-methyl-2,4-dioxo-4-(3-trifluoromethyl-phenyl)-butyric acid methyl ester. In analogy to the procedure described in Example 16A], crude 3-methyl-2,4-dioxo-4-(3-trifluoromethyl-phenyl)-butyric acid methyl ester and methylhydrazine gave after purification by flash column chromatography (n-heptane/AcOEt 2:1) 79.2 mg (3%) of the title compound as a rose powder. MS: 299.1 (MH+).

Workup

  1. customgave
  2. customafter purification by flash column chromatography (n-heptane/AcOEt 2:1) 79.2 mg (3%) of the title compound as a rose powder

Sources & evidence

ORD record
ord-606527c9217d4d3e9ca1f41f096ded8b
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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