N-bromobutanimide → HCID 117769865, compound

HRID 1526294Notes

Reaction equation

HRID 1526294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[C:4](=[O:15])[C:3]=1[C:16]#[N:17].[Br:18]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:18][C:7]1[C:2]([Cl:1])=[C:3]([C:16]#[N:17])[C:4](=[O:15])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 117770476HCID 117770476, compound

Product 1

HCID 117769865HCID 117769865, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-1-(2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step D of Example 1 (4.00 g) in N,N-dimethylformamide (33 mL) was added N-bromosuccinimide (3.49 g) at 50° C. The reaction mixture was heated at 50° C. for 6 hr, cooled to room temperature, and diluted with water. The resulting solid was collected by filtration, and washed with acetonitrile. The solid was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.30 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with acetonitrile
  4. customThe solid was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ac53d931982b4c28844732a2c7b95391
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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