2-Methylacetophenone → N'-(1-o-tolyl-ethylidene)-hydrazinecarboxylic acid ethyl ester

HRID 1795252Notes

Reaction equation

HRID 1795252 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH3:9].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[NH:12][NH2:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:11]([NH:12][N:13]=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH3:9])=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 113402-MethylacetophenoneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 72765635N'-(1-o-tolyl-ethylidene)-hydrazinecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2′-methylacetophenone (0.98 ml, 7.4 mmol), ethyl carbazate (0.81 g, 7.8 mmol) and p-toluenesulfonic acid monohydrate (70 mg, 0.37 mmol) in toluene (30 ml) was heated at reflux temperature with a Dean-Stark apparatus for 2 h. Solvent evaporation and flash chromatography (silica gel, hexane-ethyl acetate, 80:20) gave N′-(1-o-tolyl-ethylidene)-hydrazinecarboxylic acid ethyl ester; 1H NMR (CDCl3, 400 MHz) δ 7.72 (bs, 1H), 7.21 (m, 4H), 4.31 (q, 2H, J=7.1 Hz), 2.37 (s, 3H), 2.17 (s, 3H), 1.34 (t, 3H, J=7.1 Hz).

Workup

  1. temperatureat reflux temperature with a Dean-Stark apparatus for 2 h
  2. customSolvent evaporation and flash chromatography (silica gel, hexane-ethyl acetate, 80:20)

Sources & evidence

ORD record
ord-a198b815bbfb440b80cf0361d6955a3d
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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