N-bromobutanimide → HCID 59612867, compound

HRID 532859Notes

Reaction equation

HRID 532859 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([CH:8]=[CH:9][CH:10]=[N:11]3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C>[Br:21][C:13]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59612868HCID 59612868, compound

Product 1

HCID 59612867HCID 59612867, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-cyclopropylquinoline (3.45 g, 19.7 mmol) and NBS (4.03 g, 22.66 mmol) in DMF (50 mL) was heated at 65° C. for 2 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was separated, dried over anhydrous Na2SO4, concentrated, and purified by chromatography with a gradient elution of 1-10% EtOAc/CH2Cl2 to yield 8-bromo-7-cyclopropylquinoline (1.75 g, 35% yield).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified by chromatography with a gradient elution of 1-10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-cf1158dfe74f4029a3770c79fc60796a
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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