Triethylamine → 2-Hydroxyquinoline

HRID 1154943Notes

Reaction equation

HRID 1154943 reaction equation
Cl[C:2]1[C:11](OCCCC(O)=O)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:19])[NH:7]2.C(N(CC)CC)C.ClC(OCC(C)C)=O.C(NC1CCCCC1)CCC>CN(C=O)C>[NH:7]1[C:8]2[C:3](=[CH:2][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][C:6]1=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24946N-ButylcyclohexanamineHCID 62365Isobutyl chloroformateHCID 20563610HCID 20563610, compound

Product 1

HCID 60382-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 Grams of 5-chloro-6-(3-carboxypropoxy)carbostyril and 2.97 ml of triethylamine are added to 100 ml of DMF, followed by dropwise addition thereto of 2.33 ml of isobutyl chloroformate under external ice cooling and agitation while maintaining the internal temperature at 0° to 10° C. After this dropwise addition, the mixture is agitated at room temperature for 1 hour, added dropwise with 2.8 g of N-n-butylcyclohexylamine and further agitated at room temperature for 3 hours. After the reaction, the solvent is distilled off and the residue is dissolved in 600 ml of chloroform, washed with diluted hydrochloric acid, aqueous K2CO3 solution and water in that order and then dried with anhydrous Na2SO4. After removing the inorganic matter by filtration, the mother liquor is concentrated and the residue is recrystallized from ethanol, resultantly obtaining 2.5 g of 5-chloro-6-[3-N-cyclohexyl-N-butylaminocarbonyl)propoxy]carbostyril in the form of colorless needle-like crystals. m.p., 178.5°-179.5° C.

Workup

  1. additionfollowed by dropwise addition
  2. additionAfter this dropwise addition
  3. stirringfurther agitated at room temperature for 3 hours
  4. customAfter the reaction
  5. distillationthe solvent is distilled off
  6. dissolutionthe residue is dissolved in 600 ml of chloroform
  7. washwashed with diluted hydrochloric acid, aqueous K2CO3 solution and water in that order
  8. dry with materialdried with anhydrous Na2SO4
  9. customAfter removing the inorganic matter
  10. filtrationby filtration
  11. concentrationthe mother liquor is concentrated
  12. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-8cc459f6a1494f47990664899cc84c0a
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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