Sodium Hydroxide → 2-Amino-5-bromo-4-methylnicotinonitrile

HRID 233590Notes

Reaction equation

HRID 233590 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.[Br:11]N1C(=O)CCC1=O.[OH-].[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([Br:11])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 103968872-Amino-4-methylpyridine-3-carbonitrile

Product 1

HCID 113218062-Amino-5-bromo-4-methylnicotinonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 8.3 grams (0.063 mole) of 2-amino-3-cyano-4-methylpyridine in 125 mL of N,N-dimethylformamide is cooled in an ice bath, and a solution of 11.2 grams (0.063 mole) of N-bromosuccinimide in 125 mL of N,N-dimethylformamide is added dropwise during a 30 minute period, while maintaining the reaction mixture temperature at about 15°-25° C. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 20 hours. After this time, the reaction mixture is poured into 1 liter of aqueous 3N sodium hydroxide. The mixture is then diluted to a volume of about 1700 mL with distilled water. A solid precipitate is collected by filtration and dried under reduced pressure, yielding 2-amino-5-bromo-3-cyano-4-methylpyridine.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature at about 15°-25° C
  2. additionUpon completion of addition
  3. filtrationA solid precipitate is collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-26c2caa684fa42fba115e34d44e109dc
Source dataset
uspto-grants-1997_01
Patent number
US05593998

Reaction notes

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