N-bromobutanimide → 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

HRID 1380134Notes

Reaction equation

HRID 1380134 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)(=[O:3])[CH3:2].[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:23][CH2:2][C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)=[O:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide3×HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

Product 1

HCID 116678678-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinolineYield 29.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

293 mg of 5-acetyl-8-benzyloxycarbostyril are dissolved in 15 ml of chloroform, and 200 mg of N-bromosuccinimide are added thereto. The mixture is refluxed for 2 hours under stirring. 300 mg of N-bromosuccinimide are added to the mixture and 4 hours after the commencement of the reaction, 100 mg of N-bromosuccinimide are further added thereto. Six hours after the reaction is started, the mixture is cooled and is allowed to stand at 20° C. for 2 days. Precipitated crystals are collected by filtration. Then, the crystals are washed with methanol and ether and then dried. 110 mg of 5-bromoacetyl-8-benzyloxycarbostyril are thereby obtained as colorless crystals. On the other hand, the filtrate is concentrated to dryness, and the residue is treated in the same manner as above, whereby 60 mg of 5-bromoacetyl-8-benzyloxycarbostyril are further recovered from the filtrate. Total yield: 170 mg (45.8%)

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. additionare further added
  3. customSix hours
  4. temperaturethe mixture is cooled
  5. customPrecipitated crystals
  6. filtrationare collected by filtration
  7. washThen, the crystals are washed with methanol and ether
  8. customdried

Sources & evidence

ORD record
ord-91cd53af7e404ff192a49bc0f45773d0
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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