N-bromobutanimide → 7-(Bromomethyl)-4-chloroquinoline-2-carbonitrile

HRID 922755Notes

Reaction equation

HRID 922755 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]#[N:14])[CH:3]=1.C1C(=O)N([Br:22])C(=O)C1>CC#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][C:4]([C:13]#[N:14])=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 597749194-Chloro-7-methylquinoline-2-carbonitrile

Product 1

HCID 667895247-(Bromomethyl)-4-chloroquinoline-2-carbonitrileYield 57.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

4-Chloro-7-methyl-2-quinolinecarbonitrile (1-5, 57 g, 0.37 mol, 1.0 equiv.), NBS (75 g, 0.42 mol, 1.14 equiv.) and benzoyl peroxide (0.8 g, 3.3 mmol, 0.01 equiv.) were stirred in CH3CN (30 ml, 12.3 M) at room temperature. After 16 h, the solvent was removed and the residue was partitioned between AcOEt and water, the organic layer was washed with water, dried over MgSO4 and filtered. After removal of the solvent, the residue was recrystallized from methanol to give 60 g of desired 7-(bromomethyl)-4-chloroquinoline-2-carbonitrile (2-4). LRMS m/z (M+H)+ 283.1 found, 282.9 required.

Workup

  1. customthe solvent was removed
  2. customthe residue was partitioned between AcOEt and water
  3. washthe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customAfter removal of the solvent
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-8372bf4412b942e7af1e3ec5bd4c880d
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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