2-Nitrobenzoyl chloride → N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-nitrobenzoyl)hydrazine

HRID 21646

Reaction equation

HRID 21646 reaction equation
[C:1]([NH:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23])([O-:19])=[O:18]>C1(C)C=CC=CC=1.O>[C:1]([N:5]([C:22](=[O:23])[C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[N+:17]([O-:19])=[O:18])[NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 118752-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 15767542N'-t-butyl-N-(2-pyridinecarbonyl)hydrazine

Product 1

HCID 15767544N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-nitrobenzoyl)hydrazineYield 22.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of N'-t-butyl-N-(2-pyridinecarbonyl)-hydrazine (1.0 g, 0.00518 mol) in 20 ml of toluene was treated dropwise simultaneously with a solution of sodium hydroxide (1.24 g of 50% aqueous solution) in 5 ml of water and 2-nitrobenzoyl chloride (0.96 g). The resulting mixture was stirred at 23° C. overnight. Water was added and the mixture was extracted with ether. A second extraction was performed with methylene chloride and the combined organic extracts were dried over magnesium sulfate. Evaporation afforded 0.4 g of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-nitrobenzoyl)hydrazine as a yellow solid: m.p. 137°-140° C.

Workup

  1. extractionthe mixture was extracted with ether
  2. extractionA second extraction
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. customEvaporation

Sources & evidence

ORD record
ord-70c0923c5e2848879bce03b94ac269c2
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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