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

HRID 651396

Reaction equation

HRID 651396 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 to yield 1-[(4-methyl)benzoyl]-2-(3-nitrobenzoyl)hydrazine as a pale yellow solid. (2.94 g, 82%). 1H MMR (DMSOd6): δ 2.40 (s, 3H), 7.35 (d, 2H), 7.86 (d, 2H), 7.87 (t, 1H), 8.37 (d, 1H), 8.45 (d, 1H), 8.76 (s, 1H), 10.58 (s, 1H), 10.90 (s, 1H).

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-77427c6459dd44348c8490a76c1c2b90
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Linked notes

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