N-bromobutanimide → 5-Bromo-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 2253331Notes

Reaction equation

HRID 2253331 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[CH:4][CH:3]=1.[Br:11]N1C(=O)CCC1=O>ClCCCl>[Br:11][C:3]1[CH:4]=[C:5]([C:9]#[N:10])[C:6](=[O:8])[NH:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 779193-Pyridinecarbonitrile, 1,2-dihydro-6-methyl-2-oxo-

Product 1

HCID 128911045-Bromo-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 181.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (26.23 g, 95.5 mmol) and N-bromosuccinimide (36.54 g, 205 mmol) in 1,2-dichloroethane (500 mL) heated to reflux for 18 hours, cooled to room temperature, and filtered. The solid was treated with water (1 L), stirred for 2 hours, filtered, washed with water, and dried under vacuum to provide 36.85 g (88%) of the desired product of sufficient purity for subsequent use. MS (DCI/NH3) m/z 230 (M+NH4)+; 1H NMR (DMSO-d6) δ 12.96 (br s, 1H), 8.34 (s, 1H), 2.36 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. filtrationfiltered
  4. additionThe solid was treated with water (1 L)
  5. filtrationfiltered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-a66866af236c40079233c6a00a732005
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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