5-Bromo-2-chloro-3-nitropyridine → 5-Bromo-2-methoxy-3-nitropyridine

HRID 1258420Notes

Reaction equation

HRID 1258420 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[CH3:12][O-:13].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([O:13][CH3:12])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 70194125-Bromo-2-chloro-3-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 156456645-Bromo-2-methoxy-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 20.0 g (84.2 mmol) 5-bromo-2-chloro-3-nitro-pyridine in 50 mL MeOH is cooled to 0° C. and 15.8 mL (84.2 mmol) of a NaOMe solution in MeOH (30%) is added drop wise. The mixture is stirred at RT over night and then stirred under reflux for 24 h. The precipitate is filtered off, suspended in water and the suspension is stirred for 1 h. The product is filtered off and dried and vacuum at 60° C. Yield: 18.7 g (95%).

Workup

  1. stirringstirred
  2. temperatureunder reflux for 24 h
  3. filtrationThe precipitate is filtered off
  4. stirringthe suspension is stirred for 1 h
  5. filtrationThe product is filtered off
  6. customdried
  7. customat 60° C

Sources & evidence

ORD record
ord-91487f7ecce843dd8aad59e824095fcd
Source dataset
uspto-grants-2013_06
Patent number
US08466162B2

Reaction notes

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