N-bromobutanimide → HCID 59612867, compound
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was quenched with saturated aqueous NaHCO3
- extractionextracted with EtOAc
- customThe organic layer was separated
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- 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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