2-Hydroxyquinoline → 8-Cyclohexylcarbonyloxy-5-(1-hydroxy-2-isopropylaminobutyl)-3,4-dihydrocarbostyril

HRID 27781

Reaction equation

HRID 27781 reaction equation
Cl.[OH:2][CH:3]([C:11]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]2[C:12]=1[CH2:13][CH2:14][C:15](=[O:22])[NH:16]2)[CH:4]([NH:7][CH:8]([CH3:10])[CH3:9])[CH2:5][CH3:6].C[O-:24].[Na+].N1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=CC1=O>CO>[CH:31]1([C:30]([O:21][C:18]2[CH:19]=[CH:20][C:11]([CH:3]([OH:2])[CH:4]([NH:7][CH:8]([CH3:10])[CH3:9])[CH2:5][CH3:6])=[C:12]3[C:17]=2[NH:16][C:15](=[O:22])[CH2:14][CH2:13]3)=[O:24])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 60382-HydroxyquinolineHCID 10942334Sodium MethoxideHCID 233421115-(1-Hydroxy-2-isopropylaminobutyl)-8-hydroxy-3,4-dihydrocarbostyril hydrochloride

Product 1

HCID 233421188-Cyclohexylcarbonyloxy-5-(1-hydroxy-2-isopropylaminobutyl)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

3.28 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxy-3,4-dihydrocarbostyril hydrochloride was dissolved in 50 ml of methanol, and a 10% methanolic solution of sodium methylate was added to the solution in an amount of 2 moles per mole of the starting carbostyril compound. The resulting mixture was concentrated to dryness, and the residue was dissolved in dimethylformamide. 1.6 g of cyclohexanecarboxylic acid chloride was added to the solution and the mixture was stirred for 2 hours at a temperature of 10° C. The reaction mixture was poured into ice-water and the mixture was extracted with chloroform. A mixture of diethyl ether and petroleum benzene was added to the extract to obtain 1.2 g of crystalline 8-cyclohexylcarbonyloxy-5-(1-hydroxy-2-isopropylaminobutyl)-3,4-dihydrocarbostyril having a melting point of 148°-149° C. (after recrystallization from chloroform-n-hexane).

Workup

  1. concentrationThe resulting mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in dimethylformamide
  3. addition1.6 g of cyclohexanecarboxylic acid chloride was added to the solution
  4. additionThe reaction mixture was poured into ice-water
  5. extractionthe mixture was extracted with chloroform
  6. additionA mixture of diethyl ether and petroleum benzene
  7. additionwas added to the
  8. extractionextract

Sources & evidence

ORD record
ord-8764f7097d814378b0920f93d835f036
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Linked notes

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