Azobisisobutyronitrile → HCID 66767297, compound

HRID 1662023Notes

Reaction equation

HRID 1662023 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]2=[O:20])=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)(Cl)Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([CH2:14][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]2=[O:20])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 58158591HCID 58158591, compound

Product 1

HCID 66767297HCID 66767297, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 1-(4-fluorophenyl)-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (0.275 g, 1 mmol), NBS (0.2 g, 1.1 mmol), AIBN (40 mg, 0.2 mmol) in CCl4 (20 mL) is heated at reflux for 3 hours. After the reaction is cooled down, morpholine (0.088 mL, 1 mmol) and K2CO3 (0.14 g, 1 mmol) are added. The reaction is stirred at RT for another 2 hours. The solvent is removed, and the residue is diluted with water (10 mL) and extracted with EtOAc (20 mL) twice. The combined organic phases are washed with saturated aqueous sodium chloride, dried, and concentrated. The residue is purified by silica gel column chromatography eluting with DCM:MeOH (from 100:1 to 50:1, containing 0.5% 2 N NH3 in MeOH), to afford the title compound (0.17 g, 47% yield). MS (m/z): 361.1 (M+H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter the reaction is cooled down
  4. customThe solvent is removed
  5. additionthe residue is diluted with water (10 mL)
  6. extractionextracted with EtOAc (20 mL) twice
  7. washThe combined organic phases are washed with saturated aqueous sodium chloride
  8. customdried
  9. concentrationconcentrated
  10. customThe residue is purified by silica gel column chromatography
  11. washeluting with DCM

Sources & evidence

ORD record
ord-02041b4bfb244dc88d34fa1de8d00c79
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

Loading…