Hydrochloric Acid → Quinoline

HRID 2255399Notes

Reaction equation

HRID 2255399 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]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 5708341Aminoquinol

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 5

HCID 62652Cuprous chlorideCatalystHCID 241BenzeneSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

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 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

  1. customat room temperature

Sources & evidence

ORD record
ord-7f5b7361cd3d4d63ac38074ab9b26349
Source dataset
uspto-grants-1993_08
Patent number
US05240934

Reaction notes

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