Water → 6-Bromo-3,4-dihydroquinolin-2(1H)-one

HRID 44172

Reaction equation

HRID 44172 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[Br:12]N1C(=O)CCC1=O.O.CCOCC>CN(C=O)C>[Br:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][C:2](=[O:11])[CH2:3][CH2:4]2

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 64796HydrocarbostyrilHCID 67184N-bromobutanimide

Product 1

HCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3,4-dihydro-1H-quinolin-2-one (10.0 g, 67.9 mmol) in 100 ml dry DMF was added dropwise a solution of N-bromosuccinimide (12.7 g, 71.3 mmol) in 150 ml dry DMF at 0° C. The mixture was stirred at 0° C. for 2 h, then 400 ml water was added and the solution was extracted with ethyl acetate (3×150 ml). The organic phase was washed with water (2×200 ml), then dried over MgSO4 and evaporated, affording a yellow solid which was purified by washing with cold ether providing pure 6-bromo-3,4-dihydro-1H-quinolin-2-one (13.6 g, 60.3 mmol, 89%) as colorless needles.

Workup

  1. extractionthe solution was extracted with ethyl acetate (3×150 ml)
  2. washThe organic phase was washed with water (2×200 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customaffording a yellow solid which
  6. customwas purified

Sources & evidence

ORD record
ord-2c76de3fb4934d3d8f7361fe1776060d
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

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