Hydrazine hydrate (1:1) → HCID 136388354, compound

HRID 396147Notes

Reaction equation

HRID 396147 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7](/[CH:9]=[N:10]/[OH:11])=O)=[CH:3][CH:2]=1.O.[NH2:13][NH2:14]>CO>[N:13](=[C:7]([C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[CH:9]=[N:10][OH:11])[NH2:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9566037Isonitrosoacetophenone

Product 1

HCID 136388354HCID 136388354, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-isonitrosoacetophenone (50 g, 335 mmol) in methanol (500 ml) was treated with hydrazine monohydrate (19.5 ml, 402 mmol). The reaction mixture was stirred at room temperature for 20 h at which time the methanol was evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 20% EtOAc in hexanes) to afford 37 g (227 mmol; 68%) of hydrazono-phenyl-acetaldehyde oxime as a white solid. δH (360 MHz; CDCl3) 7.22-7.42 (3H, m, aromatics), 7.42-7.60 (2H, m, aromatics), 7.99 (2H, br s, NH2), 8.26 (2H, br s, ArC(NNH2)CHNOH); m/z (ES+) 164 (M++H, 100%).

Workup

  1. customwas evaporated in vacuo
  2. customThe residue was purified by flash chromatography (SiO2; 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-aa3cfcc1223f420f883005a21b58c9ec
Source dataset
uspto-grants-2003_08
Patent number
US06608062B1

Reaction notes

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