8-Hydroxyquinoline → HCID 15269575, compound

HRID 263966Notes

Reaction equation

HRID 263966 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:24][C:25](=[O:27])[CH3:26]>C1COCC1>[O:27]=[C:25]([CH3:26])[CH2:24][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 19238-HydroxyquinolineHCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 11430Potassium Carbonate

Product 1

HCID 15269575HCID 15269575, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Hydroxyquinoline (0.73 g, 5 mmol), potassium carbonate (0.69 g, 5 mmol) and dry N,N-dimethylformamide (DMF) (40 ml) were stirred at room temperature for 30 min. To this solution was added chloroacetone (0.46 g, 5 mmol) in dry THF (10 ml) in one portion. The resulting mixture was stirred at room temperature for 24 h. (monitored by TLC) and then poured into ice water (100 ml). The pale yellow solid thus obtained was collected and crystallized from dichloromethane and ether to afford 8-(2-oxopropoxy)quinoline (7a) (0.68 g, 67%) as a pale yellow needle crystal. mp: 58°-59° C.; 1H-NMR (CDCl3): δ2.32 (s, 3H, CH3), 4.88 (s, 2H, OCH2), 6.88-8.97 (m, 6H, Ar--H).

Workup

  1. customThe pale yellow solid thus obtained
  2. customwas collected
  3. customcrystallized from dichloromethane and ether

Sources & evidence

ORD record
ord-ec1086828b0947c9b964f33007ccc5ce
Source dataset
uspto-grants-1997_07
Patent number
US05646164

Reaction notes

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