Water → HCID 22341584, compound

HRID 584746Notes

Reaction equation

HRID 584746 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][NH:10][C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.O>C1(C)C=CC=CC=1>[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:9]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:10][C:11]([NH2:13])=[O:12])=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 22341576HCID 22341576, compound

Product 1

HCID 22341584HCID 22341584, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-(6-methoxypyridin-3-yl)hydrazinecarboxamide (17 g, 93.3 mmol) in 100 mL of toluene, pyridine (15.1 mL, 187 mmol) and then a solution of 4-methoxybenzoyl chloride (15.9 g, 93.3 mmol) in 50 mL of toluene were added. The mixture was refluxed with stirring for 1 hour. After cooling at 80° C., 75 mL of water was added to the mixture. After vigorous shaking, an insoluble material was isolated by filtration, washed with water and toluene, dried in vacuo to give 2-(4-methoxybenzoyl)-2-(6-methoxypyridin-3-yl)hydrazinecarboxamide (8.5 g, 28.8% yield).

Workup

  1. temperatureThe mixture was refluxed
  2. customAfter vigorous shaking, an insoluble material was isolated by filtration
  3. washwashed with water and toluene
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c31f92b27b22404ab37d5f11590e3433
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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