Sodium Hydroxide → N'-t-butyl-N-benzoyl-N'-isonicotinoylhydrazine

HRID 21643

Reaction equation

HRID 21643 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[C:1]([N:5]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 299436N'-tert-butylbenzohydrazideHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 15767540N'-t-butyl-N-benzoyl-N'-isonicotinoylhydrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
23 °C

Procedure

N'-t-butyl-N-benzoylhydrazine (1.0 g, 0.0052 mol) was suspended in 20 ml of toluene. Isonicotinoyl chloride hydrochloride (0.93 g, 0.0052 mol) was added and then a solution of sodium hydroxide (1.25 g of 50% aqueous NaOH) in 5 ml of water was added dropwise. After stirring at 23° C. for 2 hours, the solids were removed by filtration, washed with water and dried in air. The crude product was chromatographed on silica gel using 5% methanol/methylene chloride as eluant to afford pure N'-t-butyl-N-benzoyl-N'-isonicotinoylhydrazine: m.p. >210° C.

Workup

  1. customthe solids were removed by filtration
  2. washwashed with water
  3. customdried in air
  4. customThe crude product was chromatographed on silica gel using 5% methanol/methylene chloride as eluant

Sources & evidence

ORD record
ord-8743c2d7a9fc42ab9163b98b5f3b12a5
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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