Hydrochloric Acid → Quinoline
Reaction equation
Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CCN(CCCC(N[C:30]1[CH:31]=[C:32](/C=C/C2C=CC=CC=2Cl)[N:33]=[C:34]2[CH:39]=[C:38](Cl)[CH:37]=[CH:36][C:35]=12)C)CC>[Cu]Cl.O1CCOCC1.O1CCCC1.C1C=CC=CC=1.C1(C)C=CC=CC=1>[N:33]1[C:34]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:30]=[CH:31][CH:32]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 5
Procedure
The reaction of substituted o-aminobenzonitrile (10) and β-ketolactone (14) can be carried out in an alcohol in the presence of an acid such as hydrochloric acid at room temperature, or in a solvent such as toluene or benzene and in the presence of a condensing agent such as p-toluenesulfonic acid under heating. The cyclization of enamine compound (15) is carried out in a solvent such as tetrahydrofuran, 1,4-dioxane, or the like in the presence of a base (e.g., potassium carbonate) and copper (I) chloride at room temperature to the refluxing temperature. The dehydration-condensation reaction of aminoquinoline compound (16) and compound (6) for producing quinoline derivative (Ia) may be carried out in the absence of a solvent, by heating the mixture to 180°-220° C. or by heating in a sealed tube at 100°-200° C. The reactive derivative of lower fatty acid to be reacted with compound (Ia) may be carboxylic acid anhydride, carboxylic acid halide, or the like, and the reaction can be effected in the presence of a base such as pyridine, triethylamine, or the like at room temperature to 100° C. ##STR8##
Workup
- customat room temperature
Sources & evidence
- ORD record
- ord-74b792ebfdc04afb8b85b72081a7ea77
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05300517
Reaction notes
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