Ammonia → 5-Methoxypyridin-3-ylamine

HRID 1511344Notes

Reaction equation

HRID 1511344 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[OH-].[Na+].[NH3:12]>[O-]S([O-])(=O)=O.[Cu+2]>[NH2:12][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 8171633-Bromo-5-methoxypyridine

Product 1

HCID 127035955-Methoxypyridin-3-ylamine

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Conditions

Temperature
135 °C

Procedure

3-Bromo-5-methoxypyridine (15 g) was added to a pressure vessel, and CuSO4 (3.9 g) and 25% aq. ammonia (150 mL) were added. The reaction mixture was stirred for 4 h at 135° C., then cooled to RT, basified with aqueous NaOH solution, and extracted with CH2Cl2. After evaporation of volatiles, 3-amino-5-methoxypyridine was obtained as yellow solid.

Workup

  1. temperaturecooled to RT
  2. extractionextracted with CH2Cl2
  3. customAfter evaporation of volatiles

Sources & evidence

ORD record
ord-1b0a5343b10646e5b5a2777042c45fa6
Source dataset
uspto-grants-2012_07
Patent number
US08212041B2

Reaction notes

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