Sodium Hydroxide → 6-Amino-3-bromo-2-methylbenzonitrile

HRID 52619Notes

Reaction equation

HRID 52619 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O.[OH-].[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:11])=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 2799732-Amino-6-methylbenzonitrile

Product 1

HCID 224657376-Amino-3-bromo-2-methylbenzonitrileYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 8.3 grams (0.063 mole) of 2-amino-6-methylbenzonitrile in 125 mL of N,N-dimethylformamide was 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 was 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 was stirred at ambient temperature for about 20 hours. After this time, the reaction mixture was poured into 1 liter of aqueous 3N sodium hydroxide. The mixture was then diluted to a volume of about 1700 mL with distilled water. A solid precipitate was collected by filtration and dried under reduced pressure, yielding 12.3 grams of 2-amino-5-bromo-6-methylbenzonitrile, mp 111°-113° C. The NMR spectrum was consistent with the proposed structure.

Workup

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

Sources & evidence

ORD record
ord-ef3af49c57ce4adbba8b16429053ccac
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Reaction notes

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