Benzylhydrazine dihydrochloride → HCID 66958280, compound

HRID 2283736Notes

Reaction equation

HRID 2283736 reaction equation
C([O-])(=O)C.[K+].[CH3:6][CH:7]([CH3:19])[CH2:8][C:9](=O)[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Na].Cl.Cl.[CH2:23]([NH:30][NH2:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)(=O)C>[CH2:23]([N:30]1[C:9]([CH2:8][CH:7]([CH3:19])[CH3:6])=[CH:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 146540Benzylhydrazine dihydrochlorideHCID 517044Potassium AcetateHCID 3006751ethyl 6-methyl-2,4-dioxoheptanoateHCID 5360545Sodium

Product 1

HCID 66958280HCID 66958280, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

Potassium acetate (49.1 g, 0.500 mol) was added with stirring to a solution of ethyl 6-methyl-2,4-dioxoheptanoate, sodium salt (44.4 g, 0.200 mol), prepared as described in Part A of Examples 1-4, in acetic acid (280 mL). The solution was cooled to 10° C., and benzylhydrazine dihydrochloride (39.0 g, 0.200 mol) was added in portions over a period of ten minutes while the reaction temperature was maintained between 10° C. and 13.5° C. The reaction was stirred for 90 minutes at between 6° C. and 13.6° C., allowed to warm to ambient temperature, stirred overnight, and concentrated under reduced pressure. The residue was partitioned between 2 M aqueous sodium carbonate (900 mL) and tert-butyl methyl ether (600 mL). The aqueous layer was extracted with tert-butyl methyl ether (2×300 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 56.6 g of ethyl 1-benzyl-5-(2-methylpropyl)-1H-pyrazole-3-carboxylate as an oil orange. The product contained 10 mol % of ethyl 2-benzyl-5-(2-methylpropyl)-2H-pyrazole-3-carboxylate.

Workup

  1. customprepared
  2. temperaturewas maintained between 10° C. and 13.5° C
  3. temperatureto warm to ambient temperature
  4. stirringstirred overnight
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was partitioned between 2 M aqueous sodium carbonate (900 mL) and tert-butyl methyl ether (600 mL)
  7. extractionThe aqueous layer was extracted with tert-butyl methyl ether (2×300 mL)
  8. dry with materialthe combined organic fractions were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-933bb1d488184a35a218ba6dd44a07da
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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