Bromine → 7-(2-Bromoacetyl)-3,4-dihydro-2(1H)-quinolinone

HRID 2291170Notes

Reaction equation

HRID 2291170 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:15]Br>C(O)(=O)C>[Br:15][CH2:2][C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 13120789HCID 13120789, compound

Product 1

HCID 131207907-(2-Bromoacetyl)-3,4-dihydro-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
20 °C

Procedure

9.45 Grams of 7-acetyl-3,4-dihydrocarbostyril was dissolved in 30 ml of glacial acetic acid with stirring at 20° C., then a mixture of 2.6 ml of bromine with 10 ml of glacial acetic acid was added dropwise at a room temperature for 30 minutes with stirring. The reaction mixture was ice-cooled to precipitate crystals, and recrystalized from 50%-ethanol aqueous solution to obtain 7-α-bromoacetyl-3,4-dihydrocarbostyril. Yield: 9.4 g. Melting point: 202°-203° C. Colorless needle-like crystals

Workup

  1. additionwas added dropwise at a room temperature for 30 minutes
  2. stirringwith stirring
  3. temperaturecooled
  4. customto precipitate crystals
  5. customrecrystalized from 50%-ethanol aqueous solution

Sources & evidence

ORD record
ord-ac1c1dca9919461981c7750cea2e5a83
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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