Azobisisobutyronitrile → HCID 23370213, compound

HRID 1901122Notes

Reaction equation

HRID 1901122 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]([C:13]2[CH:17]=[CH:16][O:15][CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([CH3:18])=[CH:8][CH:9]=2)[N:4]=1)#[N:2].C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:18][C:7]1[CH:6]=[C:5]2[C:10]([C:11]([C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)=[CH:12][C:3]([C:1]#[N:2])=[N:4]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 233701724-(3-Furanyl)-7-methyl-2-quinolinecarbonitrile

Product 1

HCID 23370213HCID 23370213, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-cyano-4-(3-furyl)-7-methylquinoline (4.2 g) in refluxing CCl4 (400 mL) was added NBS (3.3 g) and AIBN (150 mg) portionwise. After 90 min., the mixture was cooled to r.t. and filtered through a pad of silica gel washing with CH2Cl2. The filtrate was concentrated and swished with Et2O for 15 h. The solid precipitate was collected and NMR analysis indicated that it contained 85% of the title compound. This material was used as such in the subsequent reactions.

Workup

  1. filtrationfiltered through a pad of silica gel washing with CH2Cl2
  2. concentrationThe filtrate was concentrated
  3. waitswished with Et2O for 15 h
  4. customThe solid precipitate was collected

Sources & evidence

ORD record
ord-6aa0bb66bbdd42ecb28e0415fcae3181
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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