N-(2-bromo-phenyl)-3-ethoxy-acrylamide → 8-Bromo-1,2-dihydroquinolin-2-one

HRID 2415890Notes

Reaction equation

HRID 2415890 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[CH:10]=[CH:11]OCC>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:9](=[O:15])[CH:10]=[CH:11]2

Participants

3

Reactant 1

HCID 68586854N-(2-bromo-phenyl)-3-ethoxy-acrylamide

Product 1

HCID 109330948-Bromo-1,2-dihydroquinolin-2-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

6 g (22.21 mmol) of N-(2-bromo-phenyl)-3-ethoxy-acrylamide are added batchwise to 30 ml of concentrated sulphuric acid (exothermic) and stirred for one hour. The reaction mixture is poured onto ice water and the precipitate formed is filtered off. The product is purified by column chromatography on silica gel (eluant: dichloromethane/ethyl acetate=3:1).

Workup

  1. additionThe reaction mixture is poured onto ice water
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. customThe product is purified by column chromatography on silica gel (eluant: dichloromethane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-42055ce2719743f388da10fbe354df72
Source dataset
uspto-grants-2004_11
Patent number
US06821967B2

Reaction notes

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