Acetone → 6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 49471Notes

Reaction equation

HRID 49471 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)=O.[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 180AcetoneHCID 80561,4-DibromobutaneHCID 53408427Tert-butyl 6-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Product 1

HCID 695151816-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterYield 63%

Procedure

To 11.6 g (46.5 mmol) 6-Hydroxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester in 200 ml acetone 18.6 g (134.8 mmol) K2CO3 (powdered) and 13.7 g (115.7 mmol) 1,4-dibromobutane were added. The mixture was stirred at reflux for 4 h and at RT over night. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. EtOAc and water were added, the inorganic phase was extracted with EtOAc and the combined organic phases were washed with water and dried over Na2SO4. The crude product was purified by column chromatography on silica gel with hexane/EtOAc 9:1 to yield 11.1 g (63%) 6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as colorless oil, MS: 383 (M, 1Br).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionEtOAc and water were added
  4. extractionthe inorganic phase was extracted with EtOAc
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customThe crude product was purified by column chromatography on silica gel with hexane/EtOAc 9:1

Sources & evidence

ORD record
ord-b642cb9e8bb4476bb6b726b9185b7462
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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