Acetone → 7-(4-Chlorobutoxy)-1,2,3,4-tetrahydroquinolin-2-one

HRID 241581

Reaction equation

HRID 241581 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][Cl:6].C(=O)([O-])[O-].[K+].[K+].[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1.CC(C)=O>CCCCCC>[Cl:6][CH2:5][CH2:4][CH2:3][CH2:2][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 104674677-(4-Chlorobutoxy)-1,2,3,4-tetrahydroquinolin-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1-bromo-4-chloro-butane (3.4 g, 20 mmol), anhydrous potassium carbonate powder (4.14 g, 30 mmol) and 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (1.63 g, 10 mmol) are added to 10 ml of acetone and reflux for 24 hours. The reaction solution is evaporated to dryness and dispersed with 20 ml of dichloromethane and 20 ml of water respectively. The organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively, dried over anhydrous magnesium sulfate, and evaporated to dryness, to obtain a light yellow powder. The resulting powder is slurried with n-hexane (20 ml×3), filtered, and dried to obtain 1.98 g of 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)-quinolinone, with a yield of 78%.

Workup

  1. temperaturereflux for 24 hours
  2. customThe reaction solution is evaporated to dryness
  3. additiondispersed with 20 ml of dichloromethane and 20 ml of water respectively
  4. extractionThe organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customto obtain a light yellow powder
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-fb3ae03c07f64429af56703797c27a50
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Linked notes

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