Hydrazine hydrate (1:1) → 3,3-dimethylbutanohydrazide

HRID 881745Notes

Reaction equation

HRID 881745 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[CH2:3][C:4](OC)=[O:5].O.[NH2:11][NH2:12]>CCO>[CH3:1][C:2]([CH3:9])([CH3:8])[CH2:3][C:4]([NH:11][NH2:12])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66298Methyl 3,3-dimethylbutyrate

Product 1

HCID 43467623,3-dimethylbutanohydrazideYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of methyl 3,3-dimethylbutanoate (500 mg, 3.84 mmol) in EtOH (12 ml) was added hydrazine monohydrate (1.87 ml, 38.4 mmol). The mixture was heated to 80° C. under reflux for overnight. The reaction was cooled back down to room temperature and concentrated to dryness affording a crude residue. The residue was dried under high vacuum to afford the title compound as crystalline solid (90 mg, 18% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.69-9.12 (s, 1H) 4.13 (br. s, 2H) 1.89 (s, 2H) 0.94 (s, 9H).

Workup

  1. temperatureunder reflux for overnight
  2. temperatureThe reaction was cooled back down to room temperature
  3. concentrationconcentrated to dryness
  4. customaffording a crude residue
  5. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-60863055d78c4c3d87c719c0ef7c7e81
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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