2,6-Dihydroxyquinoline → HCID 13020228, compound

HRID 1277421Notes

Reaction equation

HRID 1277421 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.[CH2:13]([N:20]1[C:24]([CH2:25][CH2:26][CH2:27]I)=[N:23][N:22]=[N:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([N:20]1[C:24]([CH2:25][CH2:26][CH2:27][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)=[N:23][N:22]=[N:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 1770652,6-DihydroxyquinolineHCID 54337875HCID 54337875, compound

Product 1

HCID 13020228HCID 13020228, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into 100 ml of ethanol, 3.22 g of 6-hydroxycarbostyril and 3.51 ml of 1,5-diazabicyclo[5,4,0]-undecene-5 (DBU) are added and refluxed under stirring. Then 100 ml of ethanol containing 7 g of 1-benzyl-5-γ-iodopropyltetrazole is added dropwise for 90 minutes. After completion of the addition, the reaction mixture is further refluxedfor 5 hours and then concentrated. The residue is extracted with 300 ml of chloroform and the chloroform layer is washed with a diluted NaOH aqueous solution, a diluted hydrochloric acid and water and dried with Na2SO4. After the removal of the solvent, the residue is recrystallized from water-containing ethanol to obtain 4 g of 6-[3-(1-benzyltetrazol-5-yl)propoxy]carbostyril in the form of colorless needle-like crystals. Melting point: 152°-154° C.

Workup

  1. temperaturerefluxed
  2. additionAfter completion of the addition
  3. concentrationconcentrated
  4. extractionThe residue is extracted with 300 ml of chloroform
  5. washthe chloroform layer is washed with a diluted NaOH aqueous solution
  6. dry with materiala diluted hydrochloric acid and water and dried with Na2SO4
  7. customAfter the removal of the solvent
  8. customthe residue is recrystallized from water-
  9. additioncontaining ethanol

Sources & evidence

ORD record
ord-6a9521382b4f492dbb47c27d33942e8b
Source dataset
uspto-grants-1981_07
Patent number
US04277479

Reaction notes

Loading…