Potassium Carbonate → 6-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinone

HRID 1277420Notes

Reaction equation

HRID 1277420 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH:19]1([N:25]2[C:29]([CH2:30][CH2:31][CH2:32]Cl)=[N:28][N:27]=[N:26]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[CH:19]1([N:25]2[C:29]([CH2:30][CH2:31][CH2:32][O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]4)=[N:28][N:27]=[N:26]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 52099225-(3-chloropropyl)-1-cyclohexyltetrazole

Product 1

HCID 130210946-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinoneYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 200 ml of dimethylformamide, 3.2 g of 6-hydroxycarbostyril, 3.3 g of potassium carbonate and 7.7 g of 1-cyclohexyl-5-γ-chloropropyltetrazole are added and stirred for 4 hours at 70° to 80° C. After the reaction is completed, dimethylformamide is removed by distillation under reduced pressure. The residue thus obtained is then extracted with 300 ml of chloroform and the chloroform layer is washed with a diluted NaOH aqueous solution and with water and next dried with Na2SO4. After removal of the drying agent by filtration, then the mother liquor is concentrated and the residue is recrystallized from chloroform to obtain 3.54 g of 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]carbostyril, in the form of colorless needle-like crystals. Melting point: 211° to 212° C.

Workup

  1. customdimethylformamide is removed by distillation under reduced pressure
  2. customThe residue thus obtained
  3. extractionis then extracted with 300 ml of chloroform
  4. washthe chloroform layer is washed with a diluted NaOH aqueous solution and with water
  5. dry with materialnext dried with Na2SO4
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe mother liquor is concentrated
  9. customthe residue is recrystallized from chloroform

Sources & evidence

ORD record
ord-56395523b1cb475792e61432a035cb2b
Source dataset
uspto-grants-1981_07
Patent number
US04277479

Reaction notes

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