Hydrazine hydrate (1:1) → 2-Cyano-2-methylpropanehydrazide

HRID 1397322Notes

Reaction equation

HRID 1397322 reaction equation
O.[NH2:2][NH2:3].[C:4]([C:6]([CH3:12])([CH3:11])[C:7](OC)=[O:8])#[N:5]>CCO.C(OCC)C>[C:4]([C:6]([CH3:12])([CH3:11])[C:7]([NH:2][NH2:3])=[O:8])#[N:5]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 109645102-Cyano-2-methyl-propanoic acid methyl ester

Product 1

HCID 866749212-Cyano-2-methylpropanehydrazideYield 39.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Hydrazine hydrate (1.8 mL, 35 mmol) was added to a solution of methyl 2-cyano-2-methylpropanoate (5.0 g, 35.0 mmol) in EtOH (5 mL), and the reaction mixture was stirred at room temperature for 1 h (monitored by TLC, eluant petroleum ether:EtOAc 7:3 v/v). The reaction mixture was diluted with diethyl ether and the precipitate formed was filtered. The clear filtrate was concentrated under reduced pressure to get 2-cyano-2-methylpropanehydrazide (1.75 g, yield 38%), which was carried through without further purification. MS (ESI) m/z: Calculated for C5H9N3O: 127.07. found: 128.2 (M+H)+.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered
  3. concentrationThe clear filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a63a9b293a464499b2f6d38b39525c92
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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