Water → HCID 117770430, compound

HRID 1526322Notes

Reaction equation

HRID 1526322 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[CH3:14])[C:4](=[O:15])[C:3]=1[C:16]#[N:17].[Br:18]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:18][C:7]1[C:2]([Cl:1])=[C:3]([C:16]#[N:17])[C:4](=[O:15])[N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 117770127HCID 117770127, compound

Product 1

HCID 117770430HCID 117770430, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-1-(2-methylcyclohexyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step E (1.14 g) in N,N-dimethylformamide (9.0 mL) was added N-bromosuccinimide (993 mg) at room temperature. The reaction mixture was heated at 50° C. for 3 hr, and cooled to room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.29 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e141f0cddc0f42c7b5e56cf22f85e5a0
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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