Azobisisobutyronitrile → HCID 90037979, compound

HRID 1055408Notes

Reaction equation

HRID 1055408 reaction equation
N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:13]N1C(=O)CCC1=O.[F:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH3:32])[C:27](=[O:33])[CH:26]=[C:25]2[CH3:34]>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:34][C:25]1[C:24]2[C:29](=[CH:30][CH:31]=[C:22]([F:21])[CH:23]=2)[N:28]([CH3:32])[C:27](=[O:33])[CH:26]=1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimide2×HCID 90037108HCID 90037108, compound

Product 1

HCID 90037979HCID 90037979, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

2,2′-Azobis(2-methylpropionitrile) (AIBN, 17.2 mg, 0.105 mmol) and N-bromosuccinimide (NBS, 97.7 mg, 0.549 mmol) were added to a suspension of 6-fluoro-1,4-dimethylquinolin-2(1H)-one (100 mg, 0.523 mmol) in CCl4 (10 mL) at 70° C. After 1 h an additional 2 eq. of NBS and 0.4 eq. of AIBN were added and the mixture heated at 70° C. for 1 h. The mixture was concentrated and the residue purified by preparative TLC to give desired the title compound (55 mg, 31%) as white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by preparative TLC
  3. customto give

Sources & evidence

ORD record
ord-690a0d36dda6407fb3731d9c987b6988
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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