Bromine → 5-Bromoacetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile

HRID 1982208Notes

Reaction equation

HRID 1982208 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[O:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[Br:14]Br>C(Cl)(Cl)Cl>[Br:14][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[O:11])[NH:8][C:9]=1[CH3:10])=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 27654765-Acetyl-2-hydroxy-6-methylnicotinonitrile

Product 1

HCID 155921665-Bromoacetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrileYield 102.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture containing 66 g of 5-acetyl-1,2 -dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile and 450 ml of chloroform was added dropwise over a period of about 40 minutes a solution containing 60.8 g of bromine in 50 ml of chloroform. The resulting mixture was stirred at room temperature for about 3 hours and then heated on a steam bath for 30 minutes during which time the red color of the reaction mixture disappeared. The reaction mixture was allowed to stir at room temperature for 1 hour and then filtered using a sintered glass funnel. The filtered product was washed with acetone and dried at 60° C. to yield 97.8 g of 5-(bromoacetyl)-1,2-dihyro-6-methyl-2-oxo-3-pyridinecarbonitrile, m.p. 212°-214° C. with decomposition. A 20 g portion of this product was dissolved in a boiling mixture of 400 ml of methanol and 200 ml of dimethylformamide, the hot solution treated with decolorizing charcoal and filtered and the filtrate concentrated on a rotary evaporator to remove the solvents. The residue was boiled with methanol and the white powdery solid was collected, washed with methanol and dried to yield 16.4 g of 5-(bromoacetyl)-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile, m.p. 213°-215° C. with decomposition.

Workup

  1. additionwas added dropwise over a period of about 40 minutes a solution
  2. temperatureheated on a steam bath for 30 minutes during which time the red color of the reaction mixture
  3. stirringto stir at room temperature for 1 hour
  4. filtrationfiltered
  5. washThe filtered product was washed with acetone
  6. customdried at 60° C.

Sources & evidence

ORD record
ord-8e35df6878e64093acee136add4ce9bc
Source dataset
uspto-grants-1986_06
Patent number
US04595762

Reaction notes

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