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

HRID 1348897Notes

Reaction equation

HRID 1348897 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-7b37d82de31d428e8316f9e9083e3e84
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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