Hydrazine hydrate (1:1) → 6-Methylpyridine-2-carbohydrazonamide

HRID 1851243Notes

Reaction equation

HRID 1851243 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=1.O.[NH2:11][NH2:12]>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([C:8](=[N:11][NH2:12])[NH2:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 741826-Methylpyridine-2-carbonitrile

Product 1

HCID 573576606-Methylpyridine-2-carbohydrazonamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.97 g (101.4 mmol) 6-methylpyridine-2-carbonitrile are dissolved in 25 mL ethanol. After addition of 36.3 mL (304.05 mmol) hydrazine hydrate (w=30%) the reaction mixture is stirred for 24 hours at room temperature. The precipitated product (K1=1.45 g) has been filtered off and the filtrate is evaporated to ⅓ of its volume. After dilution with water the reaction mixture is extracted three times with ethyl acetate. The combined organic extracts are washed with brine and dried (Na2SO4). The solvent has been removed yielding a K2 (11.11 g) of the desired product. The overall yield is 78.9%.

Workup

  1. filtrationThe precipitated product (K1=1.45 g) has been filtered off
  2. customthe filtrate is evaporated
  3. extractionAfter dilution with water the reaction mixture is extracted three times with ethyl acetate
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent has been removed

Sources & evidence

ORD record
ord-f60331f5ef99493cb92f950da32f6571
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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