Potassium Hydroxide → 6-Bromo-5-chloropyridin-2-amine

HRID 2420877Notes

Reaction equation

HRID 2420877 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)OC)[CH:5]=[CH:4][C:3]=1[Cl:13].[OH-].[K+]>CO.O>[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[Cl:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59165912Methyl 6-bromo-5-chloropyridin-2-ylcarbamate

Product 1

HCID 534011936-Bromo-5-chloropyridin-2-amineYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 6-bromo-5-chloropyridin-2-ylcarbamate (1.1 g, 4.1 mmol) in methanol (50 mL) was added KOH (700 mg, 13 mmol) at room temperature. The mixture was heated at reflux for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (20 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by column chromatography on silica gel (5% to 10% EtOAc in petroleum ether) to give 6-bromo-5-chloropyridin-2-amine (700 mg, 81%). 1H NMR (400 MHz, CDCl3) □ 7.54 (d, J=8.0 Hz, 1H), 6.41 (d, J=8.4 Hz, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hr
  3. extractionextracted with ethyl acetate (20 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated under vacuum
  6. customThe residue was purified by column chromatography on silica gel (5% to 10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-a2f570122f1a4c2692ba385cc52277de
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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