Pyridine → HCID 15168935, compound

HRID 1078554Notes

Reaction equation

HRID 1078554 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[OH:18])=[O:9])=[CH:6][C:5]([N+:19]([O-:21])=[O:20])=[CH:4][N:3]=1.N1C=CC=CC=1>O>[N+:19]([C:5]1[CH:4]=[N:3][C:2]2[O:18][C:12]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=3[NH:10][C:8](=[O:9])[C:7]=2[CH:6]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 1049PyridineHCID 15168934HCID 15168934, compound

Product 1

HCID 15168935HCID 15168935, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-5-nitro-N-(3-hydroxytol-4-yl)-3-pyridinecarboxamide (6.3 g, 0.02 mol) and pyridine (100 ml) was heated under argon at 90° C. for 2.5 hours. The cooled solution was diluted with water and the yellow-orange precipitate collected and washed with water. The solid was then stirred in hot water (100 ml) for 45 min., filtered and washed with ethanol and ether to give 4.3 g of a tan-brown solid. Recrystallization from dimethylformamide/water afforded 3.76 g (69% of theory) of product.

Workup

  1. customthe yellow-orange precipitate collected
  2. washwashed with water
  3. filtrationfiltered
  4. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-b60f204d8643434ca12004f710475706
Source dataset
uspto-grants-1996_08
Patent number
US05550122

Reaction notes

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