Hydrazine hydrate (1:1) → methyl 4-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoate

HRID 541451Notes

Reaction equation

HRID 541451 reaction equation
[CH:1]1([C:5]2[C:14]([C:15](=O)[CH2:16][C:17](=O)[CH2:18][CH3:19])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[NH2:23][NH2:24].O>CO>[CH:1]1([C:5]2[C:14]([C:15]3[CH:16]=[C:17]([CH2:18][CH3:19])[NH:24][N:23]=3)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68288990Methyl 4-cyclobutyl-2-methyl-5-(3-oxopentanoyl)benzoate2×

Product 1

HCID 68288367methyl 4-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoateYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-cyclobutyl-2-methyl-5-(3-oxopentanoyl)benzoate (compound 445.1, 300 mg, 0.990 mmol, 1.00 equiv) in methanol (15 mL) was added NH2NH2.H2O. The resulting solution was stiffed for 1.5 h at 80° C. in an oil bath, and then concentrated under reduced pressure. The residue was diluted with 100 mL of ethyl acetate, then washed with 3×100 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:5) as eluent to yield 188 mg (64%) of the title compound as a yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with 100 mL of ethyl acetate
  3. washwashed with 3×100 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-44bd24c355f34c519c119474a5a72964
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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