Ammonium Chloride → 5-Bromo-2-methoxypyridin-3-amine

HRID 557535Notes

Reaction equation

HRID 557535 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 156456645-Bromo-2-methoxy-3-nitropyridine

Product 1

HCID 447548695-Bromo-2-methoxypyridin-3-amineYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
95 °C

Procedure

In a 500 mL, round-bottomed, single-necked flask equipped with a magnetic stirring bar was placed 5-bromo-2-methoxy-3-nitropyridine (15) (20.0 g, 0.086 mol), Fe (20.0 g, 0.36 mol), and NH4Cl (20.0 g, 0.36 mol) in EtOH/H2O (150 mL, 1:1). After heating at 95° C. for 1 h, the reaction mixture was filtered through a pad of Celite. The filtrate was concentrated to give 16.5 g (95%) of 5-bromo-2-methoxypyridin-3-amine (16) as a solid.

Workup

  1. customIn a 500 mL, round-bottomed, single-necked flask equipped with a magnetic stirring bar
  2. filtrationthe reaction mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-43f9315eebf84cdc99d7795001902f5c
Source dataset
uspto-grants-2011_11
Patent number
US08058446B2

Reaction notes

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