Ethyl Bromide → 6-Bromo-1-ethyl-3,4-dihydroquinolin-2(1H)-one

HRID 44174

Reaction equation

HRID 44174 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH3:13][C:14]([O-])(C)C.[K+].C(Br)C>CN(C=O)C.Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:13][CH3:14])[C:7](=[O:12])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 669113046-Bromo-1-ethyl-3,4-dihydroquinolin-2(1H)-oneYield 69%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-bromo-3,4-dihydro-1H-quinolin-2-one (750 mg, 3.32 mmol) in 20 ml dry DMF was added potassium tert-butylate (804 mg, 6.64 mmol). After the mixture was stirred for 30 min at room temperature, a solution of ethyl bromide (724 mg, 6.64 mmol) in 10 ml dry DMF was added. Following overnight stirring, the mixture was diluted with 150 ml 1 N HCl. Extraction with ethyl acetate (2×100 mL) followed by washing of the organic extracts with water and brine, drying over MgSO4 and removal of the solvent in vacuo gave a light yellow solid. Purification by flash chromatography (hexanes/ethyl acetate, 1/1, Rf=0.52) gave 6-bromo-1-ethyl-3,4-dihydro-1H-quinolin-2-one (583 mg, 2.29 mmol, 59%) as a colorless solid.

Workup

  1. waitFollowing overnight
  2. stirringstirring
  3. extractionExtraction with ethyl acetate (2×100 mL)
  4. washby washing of the organic extracts with water and brine
  5. dry with materialdrying over MgSO4 and removal of the solvent in vacuo
  6. customgave a light yellow solid
  7. customPurification by flash chromatography (hexanes/ethyl acetate, 1/1, Rf=0.52)

Sources & evidence

ORD record
ord-1ce98bb2e7c3438e8b24f96ce768f4f9
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

Loading…