Hydrazine hydrate (1:1) → 4-(Pyridin-2-yl)benzaldehyde hydrazone

HRID 1857790Notes

Reaction equation

HRID 1857790 reaction equation
O.[NH2:2][NH2:3].[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1>CO>[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[N:2][NH2:3])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15152404-Pyridin-2-ylbenzaldehyde

Product 1

HCID 679245134-(Pyridin-2-yl)benzaldehyde hydrazoneYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 80% hydrazine hydrate (1.64 g, 26.2 mmol) and methanol (5.0 ml) was dropwise added a solution of 4-(pyridin-2-yl)benzaldehyde (1.5 g, 8.2 mmol) in methanol (5.0 ml) at 25° C. over 10 minutes. After the dropwise addition, the mixture was stirred for 30 minutes. Methanol and excess hydrazine hydrate were evaporated under reduced pressure. The residue was crystallized and 4-(pyridin-2-yl)benzaldehyde hydrazone was obtained as crude crystals at a yield of 1.6 g (yield:100%). The percentage of the area of 4-(pyridin-2-yl)benzaldehyde hydrazone in the crude crystals as determined by liquid chromatography was 94.30%.

Workup

  1. additionAfter the dropwise addition
  2. customMethanol and excess hydrazine hydrate were evaporated under reduced pressure
  3. customThe residue was crystallized

Sources & evidence

ORD record
ord-6dfadd60d3324e2da4eeefe4bdd20819
Source dataset
uspto-grants-2000_11
Patent number
US06147218

Reaction notes

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