Hydrazine → 4-Hydroxycyclohexanecarbohydrazide

HRID 1174661Notes

Reaction equation

HRID 1174661 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10]CC)=O)[CH2:4][CH2:3]1.[NH2:13][NH2:14]>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([NH:13][NH2:14])=[O:10])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 575167944-Hydroxycyclohexanecarbohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of ethyl 4-hydroxycyclohexanecarboxylate (2.0 g, 12 mmol) and hydrazine (1.5 g, 46 mmol) in methanol (20 mL) was stirred at 55° C. for 4 h and then cooled to room temperature (about 25° C.). After cooling, the solvent and excess hydrazine were removed by distillation under reduced pressure to provide a residue. The residue was co-evaporated with methanol (2×), and was then dried under high vacuum to provide the crude product 4-hydroxycyclohexanecarbohydrazide, which was used in the next synthesis step without further purification. LCMS: (M+H)+=155.2.

Workup

  1. temperaturecooled to room temperature (about 25° C.)
  2. temperatureAfter cooling
  3. customthe solvent and excess hydrazine were removed by distillation under reduced pressure
  4. customto provide a residue
  5. customwas then dried under high vacuum

Sources & evidence

ORD record
ord-7d66d654d234400f9660538279b2c3e5
Source dataset
uspto-grants-2010_11
Patent number
US07838544B2

Reaction notes

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