Potassium Hydroxide → HCID 118113969, compound

HRID 2178404Notes

Reaction equation

HRID 2178404 reaction equation
Cl.[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[O:11][CH3:12].Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([I:23])=[CH:16][N:15]=1.[OH-].[K+]>C(#N)C>[I:23][C:17]1[CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:14]([NH:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([OH:2])=[C:4]([O:11][CH3:12])[CH:5]=2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)HCID 15142942-Chloro-5-iodo-3-nitropyridine

Product 1

HCID 118113969HCID 118113969, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 4-hydroxy-3-methoxybenzylamine hydrochloride (1.32 g, 6.82 mmol) and 2-chloro-5-iodo-3-nitropyridine (2.00 g, 6.82 mmol) in acetonitrile (20 mL) was added N,N-disopropylethylamine (5.96 ml, 34.10 mmol) The suspension was stirred and heated to 100° C. After 1 h, the mixture was allowed to cool to room temperature, and 2N aqueous potassium hydroxide solution (0.68 mL) was added. The mixture was concentrated to provide 4-(((5-iodo-3-nitropyridin-2-yl)amino)methyl)-2-methoxyphenol as an impure solid.

Workup

  1. temperatureto cool to room temperature
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-7338dc3e2fbb4bb0aa386fd88d4990cb
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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