Water → N'-t-butyl-N-(2-hydroxymethylbenzoyl)hydrazine

HRID 21621

Reaction equation

HRID 21621 reaction equation
[C:1]([NH:5][NH2:6])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:9]1([C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][O:11]1)=[O:10].O>C(O)C>[C:1]([NH:5][NH:6][C:9](=[O:10])[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:12][OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6885PhthalideHCID 14798Sodium HydroxideHCID 81890tert-Butylhydrazine

Product 1

HCID 19368051N'-t-butyl-N-(2-hydroxymethylbenzoyl)hydrazineYield 13.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

t-Butylhydrazine (0.1 mol) in 75 ml ethanol was treated with 50% aqueous sodium hydroxide (0.11 mol). Phthalide (0.1 mol) was added and the mixture was refluxed for 5 days. After cooling, water was added and the crude product was isolated by filtration. Filtration through silica gel afforded N'-t-butyl-N-(2-hydroxymethylbenzoyl)hydrazine (3.0 g): m.p. 116°-118° C.

Workup

  1. temperaturethe mixture was refluxed for 5 days
  2. temperatureAfter cooling
  3. customthe crude product was isolated by filtration
  4. filtrationFiltration through silica gel

Sources & evidence

ORD record
ord-70f1a15021854145b1b9c22f57f6e88f
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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