Water → 5-Amino-2-bromo-3-methylpyridine

HRID 1748620Notes

Reaction equation

HRID 1748620 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.C(O)(C)C.O.C(=O)([O-])[O-].[K+].[K+]>[Fe].C(O)(=O)C>[NH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 52004662-Bromo-3-methyl-5-nitropyridine

Product 1

HCID 123624465-Amino-2-bromo-3-methylpyridineYield 77.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-bromo-3-methyl-5-nitropyridine (10.01 g), isopropanol (130 ml), water (26 ml) and iron (12.9 g) was added acetic acid (5.27 ml), and stirred at 80° C. for 3.5 hours. To the reaction solution was added potassium carbonate (13.37 g), filtered through Celite, then extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The precipitated solid was collected by filtration to give 5-amino-2-bromo-3-methylpyridine (6.66 g) as a gray solid. MS (ESI) m/z: 187, 189 (M+H)+.

Workup

  1. filtrationfiltered through Celite
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ef475d9bc0564824b654722041e2838c
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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