2-Amino-4-methylpyridine → 2-Amino-5-bromo-4-methylpyridine

HRID 1740947Notes

Reaction equation

HRID 1740947 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Br:9]Br>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 24408Bromine

Product 1

HCID 8176952-Amino-5-bromo-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
17.5 °C

Procedure

To a solution of 2-amino-4-picoline (20 g, 0.185 mol) in glacial acetic acid (185 mL) was added bromine (12.5 mL, 0.243 mol) dropwise with stirring while maintaining the internal temperature between 15-20° C. by cooling in an ice bath. After the addition was completed, the reaction was stirred for 1 h. The resulting solid was filtered, washed with water, and treated with dilute aqueous sodium hydroxide. The remaining white solid was filtered, washed with water and then hexane. Recrystallization from diethyl ether-cyclohexane afforded the title compound; yield 8.1 g (23%).

Workup

  1. temperatureby cooling in an ice bath
  2. additionAfter the addition
  3. stirringthe reaction was stirred for 1 h
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. additiontreated with dilute aqueous sodium hydroxide
  7. filtrationThe remaining white solid was filtered
  8. washwashed with water
  9. customRecrystallization from diethyl ether-cyclohexane

Sources & evidence

ORD record
ord-5d174fe9e1d24b2ea4fdf3844c2aa73f
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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