Sodium Hydroxide → 2-Bromo-5-methylpyridin-4-amine

HRID 1522556Notes

Reaction equation

HRID 1522556 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][N+:3]=1[O-].[OH-].[Na+]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:11])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 6160962-Bromo-5-methyl-4-nitropyridin-1-ium-1-olate

Product 1

HCID 126437092-Bromo-5-methylpyridin-4-amineYield 53.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-5-methyl-4-nitropyridine 1-oxide (0.5 g, 2.146 mmol) in acetic acid (10 mL) at 25° C. was added iron (0.479 g, 8.58 mmol). The reaction was heated to 100° C. for 30 minutes, then cooled to room temperature, poured into NaOH (1N, 30 mL), extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated to dryness to give 2-bromo-5-methylpyridin-4-amine (213 mg, 53.1% yield) as a brown solid which was used without further purification. ESI-MS: m/z 187.0 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-88948a65f09841b2aabc22afb0fe13bb
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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