Methylhydrazine → ethyl 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)propanoate

HRID 220462Notes

Reaction equation

HRID 220462 reaction equation
[C:1]([CH:4]([C:12](=O)[CH3:13])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH3:2].[CH3:15][NH:16][NH2:17]>C(O)(=O)C>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C:4]1[C:12]([CH3:13])=[N:17][N:16]([CH3:15])[C:1]=1[CH3:2])[CH3:11]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 2733934Hexanoic acid, 4-acetyl-5-oxo-, ethyl ester

Product 1

HCID 16394809ethyl 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)propanoateYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolve ethyl 4-acetyl-5-oxohexanoate (2.00 g, 9.99 mmol) in acetic acid (21 mL). Add methyl hydrazine (589 μL, 10.99 mmol) and stir at room temperature for 18 hr. Concentrate and dissolve residue in ethyl acetate. Wash ethyl acetate layer with saturated aqueous sodium bicarbonate solution. Extract aqueous layer twice with ethyl acetate, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 100% ethyl acetate:hexanes) to give 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-propionic acid ethyl ester (1.95 g, 93%). MS (ES): m/z=211 [M+H]+.

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve residue in ethyl acetate
  3. dry with materialExtract aqueous layer twice with ethyl acetate, dry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 0:100 to 100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-000c6f90b8f246098496a859eabe70f4
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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