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

HRID 1531392Notes

Reaction equation

HRID 1531392 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][B:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[O:4][CH2:3]1.O.[NH2:18][NH2:19]>CO.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:16])[O:6][B:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH:18][NH2:19])=[O:12])=[CH:9][CH:8]=2)[O:4][CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21253982HCID 21253982, compound

Product 1

HCID 212539774-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzohydrazideYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

58.5 g (250 mmol) of 4-(5,5-dimethyl-1,3,2-dioxaborolan-2-yl)benzoic acid are dissolved in 250 ml of methanol, and 12.5 g (250 mmol) of hydrazine hydrate and 1.5 g (12.5 mmol) of 4-dimethylaminopyridine are added. The solution is refluxed for 12 hours. Removal of 200 ml of methanol by distillation gives 44.6 g (180 mmol, 72%) of product.

Workup

  1. temperatureThe solution is refluxed for 12 hours
  2. customRemoval of 200 ml of methanol
  3. distillationby distillation

Sources & evidence

ORD record
ord-1104d07373b14f7dbb2b596d0149c5c9
Source dataset
uspto-grants-2001_03
Patent number
US06197967B1

Reaction notes

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