Hydrazine hydrate (1:1) → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide

HRID 1531390Notes

Reaction equation

HRID 1531390 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][CH:10]=2)[O:3]1.O.[NH2:21][NH2:22]>CO>[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:21][NH2:22])=[O:14])=[CH:11][CH:10]=2)[O:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 212539794-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazideYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g (76 mmol) of methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate are dissolved in 150 ml of methanol, 6 g (120 mmol) of hydrazine hydrate are added, and the mixture is refluxed for 12 hours. Removal of 120 ml of methanol by distillation gives 19.8 g (75 mmol, 98%) of product. The compounds of the formula (III) are obtained analogously using the compounds shown in Table 3.

Workup

  1. temperaturethe mixture is refluxed for 12 hours
  2. customRemoval of 120 ml of methanol
  3. distillationby distillation

Sources & evidence

ORD record
ord-fab34166e87f4e129b9515bf19103abb
Source dataset
uspto-grants-2001_03
Patent number
US06197967B1

Reaction notes

Loading…