Potassium Hydroxide → 5-Bromo-2-nitropyridin-3-amine

HRID 1294066Notes

Reaction equation

HRID 1294066 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:11]C(OCC)=O)[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[OH-].[K+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 15645653HCID 15645653, compound

Product 1

HCID 589057095-Bromo-2-nitropyridin-3-amineYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-3-(ethoxycarbonyl)amino-2-nitropyridine (1.57 g, 5.4 mmol) in ethanol (2.5 mL) was added KOH (813 mg, 14.5 mmol) in water (12.5 mL) and stirred at 90° C. for 1 hr then at room temperature for 1 hr. The mixture was added water. The formed precipitate was collected by filtration, washed with water then dried under reduced pressure to give the title compound (1.08 g, 92%): MS m/e 216, 218 (M−1).

Workup

  1. waitat room temperature for 1 hr
  2. filtrationThe formed precipitate was collected by filtration
  3. washwashed with water
  4. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-12f5763bf6c048bfa2107415c190cb93
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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