Dimethylformamide → Quinoline-3-carbonyl Chloride
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[CH:2]=1.CN(C)C=O.C(Cl)(=O)C([Cl:22])=O>ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([Cl:22])=[O:13])[CH:2]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of quinoline-3-carboxylic acid (0.1 g, 0.57 mmol) in dichloromethane (1.5 ml) is treated with dimethylformamide (0.02 ml) and then oxalylchloride (0.1 ml, 1.15 mmol). The reaction mixture is stirred under argon at ambient temperature for 1.6 hours, then evaporated to afford quinoline-3-carbonyl chloride as a crude pale yellow solid. The crude material is suspended in dichloromethane (2.0 ml) and treated with bromopropylamine hydrobromide (0.125 g, 0.57 mmol) and triethylamine (0.42 ml, 3 mmol). The reaction mixture is stirred at ambient temperature for 3.25 hours, then quenched with water and partitioned between aqueous NaHCO3 solution and dichloromethane. The organic phase is washed with NaHCO3 solution and brine, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution ethyl acetate) to afford quinoline-3-carboxylic acid (3-bromopropyl)-amide. [MH]+ 292.9.
Workup
- customevaporated
Sources & evidence
- ORD record
- ord-14cc9f054b6b469595dd44ca58b67f87
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288537B2
Reaction notes
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