Water → 5-Bromo-2-ethoxypyridin-3-amine

HRID 1052519Notes

Reaction equation

HRID 1052519 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[Cl-].[NH4+].O>CCO.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 582557825-Bromo-2-ethoxy-3-nitropyridine

Product 1

HCID 532116995-Bromo-2-ethoxypyridin-3-amineYield 83%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

5-Bromo-2-ethoxy-3-nitropyridine (805 mg, 3.26 mmol), ammonium chloride (732 mg, 13.68 mmol) and powdered iron (764 mg, 13.68 mmol) were suspended in EtOH (3.4 ml) and water (3.4 ml) and stirred for 90 min at 100° C. The reaction mixture was filtered through Celite after dilution with EtOH. The solvent was evaporated under reduced pressure, water was added and the mixture neutralised to pH=6 with sodium carbonate and extracted with dichloromethane (×3). The organic phase was washed successively with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 708 mg (83% yield, 92% purity) of the titled compound were obtained and used in the next synthetic step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite after dilution with EtOH
  2. customThe solvent was evaporated under reduced pressure, water
  3. additionwas added
  4. extractionextracted with dichloromethane (×3)
  5. washThe organic phase was washed successively with water and brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-46a3667688f6494dba172097cb605658
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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