Hydrogen Bromide → HCID 15290773, compound

HRID 2209962Notes

Reaction equation

HRID 2209962 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8](=[O:16])[CH:7]=1.[BrH:17]>>[Br:17][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8](=[O:16])[CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 19379706HCID 19379706, compound

Product 1

HCID 15290773HCID 15290773, compoundYield 61.3%

Procedure

4-(4-hydroxybutyl)-2(1H)-quinolinone (1 g, 4.60 mmol) was suspended in 47%hydrobromic acid solution (20 ml) and the mixture was refluxed for 16 hours. The reaction mixture was cooled in ice bath and the separated solid was filtered off by aspiration. The residue was washed with water and recrystallized with methanol (with treatment with activated carbon) to give the entitled compound (II-4) as white crystals (790 mg, yield 61.3%, mp 156°-158 ° C. (methanol)).

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureThe reaction mixture was cooled in ice bath
  3. filtrationthe separated solid was filtered off by aspiration
  4. washThe residue was washed with water
  5. customrecrystallized with methanol (with treatment with activated carbon)
  6. customto give the entitled compound (II-4) as white crystals (790 mg, yield 61.3%, mp 156°-158 ° C. (methanol))

Sources & evidence

ORD record
ord-ea04c69b2a6b4e699a6e5d2157656f66
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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