Sodium Hydroxide → 5-bromo-2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine

HRID 53541Notes

Reaction equation

HRID 53541 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([N:11]([CH3:13])[CH3:12])[N:3]=1.[Br:14]Br.[OH-].[Na+]>C(O)(=O)C.O>[Br:14][C:5]1[C:6]([CH3:10])=[C:7]([C:8]#[N:9])[C:2]([Cl:1])=[N:3][C:4]=1[N:11]([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 199600452-Chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine

Product 1

HCID 199600285-bromo-2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridineYield 98.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine (0.98 g) in acetic acid (10 mL) was added bromine (0.9 g) in acetic acid (1 mL). The reaction mixture was stirred at room temperature for 20 minutes and then warmed to 60° C. for 5 minutes. After cooling to room temperature the mixture was poured into a solution of sodium hydroxide (8 g) in water (100 mL). The mixture was extracted with chloroform (3×30 mL). The combined organic phase was washed, dried, and evaporated to give 1.36 g of the title compound, suitable for use in the next reaction.

Workup

  1. temperaturewarmed to 60° C. for 5 minutes
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionThe mixture was extracted with chloroform (3×30 mL)
  4. washThe combined organic phase was washed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-f41d23391e474101991fe6e5a3777f55
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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