8-hydroxyquinolin-2(1H)-one → HCID 12674740, compound

HRID 2398943Notes

Reaction equation

HRID 2398943 reaction equation
[Br:1][CH:2]([CH2:6][CH3:7])[C:3](Br)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[OH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[NH:21][C:20](=[O:23])[CH:19]=[CH:18]2>C(=S)=S>[Br:1][CH:2]([CH2:6][CH3:7])[C:3]([C:16]1[CH:15]=[CH:14][C:13]([OH:12])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:23])[NH:21]2)=[O:4]

Participants

5

Reactant 3

HCID 972508-hydroxyquinolin-2(1H)-oneHCID 1172932-Bromobutanoyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12674740HCID 12674740, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
50 °C

Procedure

50 g of α-bromobutyric acid bromide (V), 50 g of anhydrous aluminum chloride and 400 ml of carbon disulfide were added to 20 g of 8-hydroxycarbostyril (VI). The resulting mixture was heated at a temperature of 50° C for 13 hours and the carbon disulfide layer was removed by decantation. Crushed ice was added to the residue to crystallize the product, and the crystals thus formed were filtered, washed with water and then recrystallized from methanol to obtain 27 g of 5-(α-bromobutyryl)-8-hydroxycarbostyril (VI) having a melting point of 218°-219° C (with coloring and decomposition).

Workup

  1. customthe carbon disulfide layer was removed by decantation
  2. additionCrushed ice was added to the residue
  3. customto crystallize the product
  4. customthe crystals thus formed
  5. filtrationwere filtered
  6. washwashed with water
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c2aa6392e0dc40198553163ade6384dd
Source dataset
uspto-grants-1977_05
Patent number
US04026897

Reaction notes

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