p-Toluenesulfonic acid → 3-Nitrosalicylic (1-phenylethylidene)hydrazide

HRID 1281660Notes

Reaction equation

HRID 1281660 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([NH:9][NH2:10])=[O:8])[C:5]=1[OH:14])([O-:3])=[O:2].[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C:18]1([C:15](=[N:10][NH:9][C:7](=[O:8])[C:6]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=[CH:12][CH:11]=2)[OH:14])[CH3:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7410AcetophenoneHCID 113676062-Hydroxy-3-nitrobenzenecarbohydrazide

Product 1

HCID 727809033-Nitrosalicylic (1-phenylethylidene)hydrazideYield 93.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 1.0 g (5 mmol) of 3-nitrosalicylohydrazide in 50 ml of anhydrous ethanol were treated with 0.6 g (5 mmol) of acetophenone and with a catalytic amount of p-toluenesulfonic acid. After the mixture had been stirred for 14 hours at approximately 20 to 25° C. and the solvent had been distilled off, 1.4 g of the title compound (90% of theory) were obtained as colorless crystals of m.p.: 163-168° C.

Workup

  1. distillationthe solvent had been distilled off

Sources & evidence

ORD record
ord-721e0148b62d4141af3a9cd7c704abed
Source dataset
uspto-grants-2002_09
Patent number
US06455515B2

Reaction notes

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