Dimethylformamide → 7-(4-Chlorobutoxy)-1H-quinolin-2-one

HRID 1500544Notes

Reaction equation

HRID 1500544 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][Cl:29]>O>[Cl:29][CH2:28][CH2:27][CH2:26][CH2:25][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 109757877-Hydroxycarbostyril

Product 1

HCID 566050407-(4-Chlorobutoxy)-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

After 7-hydroxy-1H-quinolin-2-one (10 g) and DMF (50 ml) were heated to approximately 30° C., an aqueous potassium carbonate solution (potassium carbonate: 8.6 g, water: 10 ml) was added. After the mixture was stirred at 30 to 40° C. for about 15 minutes, 1-bromo-4-chlorobutane (14.3 ml) was added and stirred at approximately 40° C. for 5 hours. Water (100 ml) was added dropwise over a period of 30 minutes or more while the temperature was maintained at 30° C. or more. After the mixture was stirred at approximately 30° C. for 30 minutes, stirring was continued at 10° C. or less for 1 hour, after which the precipitated crystals were collected by filtration. After methanol (100 ml) was added to the precipitated crystals, the mixture was stirred under reflux to ensure dissolution. This solution was cooled and stirred at 30 to 40° C. for 30 minutes and then at 5° C. or less for about 1 hour, after which the precipitated crystals were collected by filtration. The crystals were dried at 60° C. to obtain 7-(4-chlorobutoxy)-1H-quinolin-2-one as white powder.

Workup

  1. stirringstirred at approximately 40° C. for 5 hours
  2. temperaturewas maintained at 30° C. or more
  3. stirringAfter the mixture was stirred at approximately 30° C. for 30 minutes
  4. stirringstirring
  5. waitwas continued at 10° C. or less for 1 hour
  6. filtrationafter which the precipitated crystals were collected by filtration
  7. additionAfter methanol (100 ml) was added to the precipitated crystals
  8. stirringthe mixture was stirred
  9. temperatureunder reflux
  10. dissolutiondissolution
  11. temperatureThis solution was cooled
  12. stirringstirred at 30 to 40° C. for 30 minutes
  13. waitat 5° C. or less for about 1 hour
  14. filtrationafter which the precipitated crystals were collected by filtration
  15. customThe crystals were dried at 60° C.

Sources & evidence

ORD record
ord-39c12c097af0447eb8d8c4245b447d6f
Source dataset
uspto-grants-2015_12
Patent number
US09206169B2

Reaction notes

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