4-Methylbenzoyl Chloride → N'-[(4-methylphenyl)carbonyl]-3-nitrobenzohydrazide

HRID 1274212Notes

Reaction equation

HRID 1274212 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([NH:9][NH2:10])=[O:8])([O-:3])=[O:2].[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:23][C:14]1[CH:19]=[CH:18][C:17]([C:20]([NH:10][NH:9][C:7](=[O:8])[C:6]2[CH:11]=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 32914983-Nitrobenzohydrazide

Product 1

HCID 4506110N'-[(4-methylphenyl)carbonyl]-3-nitrobenzohydrazide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-nitrobenzhydrazide (2.16 g, 11.92 mmol) in pyridine (40 ml) cooled to 0° C. in an ice bath is added dropwise p-toluoyl chloride (1.94 g, 11.92 mmol). The mixture is allowed to warm to room temperature and stirred for 12 hours. The mixture is quenched with 350 mL of water and stirred for thirty minutes. The precipitate is filtered and dried in a vacuum oven :o yield 1-[(4-methyl)benzoyl]-2-(3-nitrobenzoyl)hydrazine as a pale yellow solid. (2.94 g, 82%).

Workup

  1. customThe mixture is quenched with 350 mL of water
  2. stirringstirred for thirty minutes
  3. filtrationThe precipitate is filtered
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-542ae09026104a4db2b4891c8d4bbdae
Source dataset
uspto-grants-2000_12
Patent number
US06156776

Reaction notes

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