Sodium Hydroxide → 2-Chloro-6-(imidazol-1-yl)-4-methylpyridine-3-carboxamide

HRID 53553Notes

Reaction equation

HRID 53553 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[N:3]=1.[OH-].[Na+].C(=O)(O)[O-:19].[Na+]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[C:7]([C:8]([NH2:9])=[O:19])=[C:6]([CH3:10])[CH:5]=[C:4]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 199600342-Chloro-3-cyano-6-(imidazol-1-yl)-4-methylpyridine

Product 1

HCID 199600712-Chloro-6-(imidazol-1-yl)-4-methylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-chloro-3-cyano-6-(imidazol-1-yl)-4-methylpyridine (2.1 g) in concentrated sulfuric acid (5 mL) was heated at 130° C. for 15 minutes. The mixture was cooled to room temperature, diluted with water (10 mL), and adjusted to pH 7 with 20% sodium hydroxide solution followed by solid sodium bicarbonate. The crystalline product was removed by filtration and dried to give 2.35 g of the title compound, suitable for use in the next reaction.

Workup

  1. customThe crystalline product was removed by filtration
  2. customdried

Sources & evidence

ORD record
ord-24e3e04e78f44c6895cfb7d951f704f4
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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