Isobutyryl chloride → isobutyric acid N'-(5-bromo-pyridin-2-yl)-hydrazide

HRID 2121628Notes

Reaction equation

HRID 2121628 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[C:19](Cl)(=[O:23])[CH:20]([CH3:22])[CH3:21]>ClCCl.CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 68901957isobutyric acid N'-(5-bromo-pyridin-2-yl)-hydrazide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred cold (0° C.) solution of 5.5 g of 5-bromo-pyridin-2-yl-hydrazine in 40 mL of dichloromethane, 30 mL of N,N-dimethylformamide, and 26 mL of N,N-diisopropylethylamine was added 3.1 ml of isobutyryl chloride dropwise. The mixture was stirred at 0° C. for 1 hour and a precipitate formed. The mixture was diluted with water and the solids were collected by filtration to give 5.9 g of isobutyric acid N′-(5-bromo-pyridin-2-yl)-hydrazide as a light yellow solid.

Workup

  1. customa precipitate formed
  2. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-82a8b104feec4f84a54f2c63772ad542
Source dataset
uspto-grants-2004_02
Patent number
US06696464B2

Reaction notes

Loading…