Potassium Hydroxide → HCID 18402944, compound

HRID 2270905Notes

Reaction equation

HRID 2270905 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.[OH-].[K+].Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=1>CS(C)=O>[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([CH:7]=1)[O:8][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 796132-Chloro-3-nitropyridineHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 18402944HCID 18402944, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-amino-2-chloro-4-fluorophenol (0.64 g), powdered potassium hydroxide (0.24 g), and 2-chloro-3-nitropyridine (0.76 g) in dimethylsulfoxide (15 ml) was heated at 110° C. with stirring for 2 hours. The solution was processed and the resulting oil chromatographed on silica gel eluting with methanol:methylene chloride, 3:97, to yield 2-(5-amino-2-chloro-4-fluorophenoxy)-3-nitropyridine (Intermediate IIa) as a yellow semi-solid (0.45 g).

Workup

  1. customthe resulting oil chromatographed on silica gel eluting with methanol

Sources & evidence

ORD record
ord-6d1dafe46d0b429eb3273f9daa37718f
Source dataset
uspto-grants-2001_12
Patent number
US06333296B1

Reaction notes

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