Ethanol → HCID 19592685, compound

HRID 613581Notes

Reaction equation

HRID 613581 reaction equation
[Cl-].[NH4+].C(O)C.[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[NH:17][C:18](=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-])=O>O.[Fe]>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([NH:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[N:9]=[CH:8][C:7]([Br:6])=[CH:16]2)=[O:28]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 19592999HCID 19592999, compound

Product 1

HCID 19592685HCID 19592685, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ammonium chloride (50.9 mg) in water (2 ml) was added ethanol (10 ml), and the mixture was stirred at 50° C. To the mixture were added 3-bromo-8-(2-nitrobenzoylamino)quinoline (590 mg) and iron (531 mg), and the mixture was refluxed for 1 hour. After filtration, the filtrate was concentrated in vacuo, and the residue was suspended in hot 80% ethanol and allowed to cool to ambient temperature. The resulting precipitates were collected by filtration to give 8-(2-aminobenzoylamino)-3-bromoquinoline (470 mg) as pale tan solid.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. temperatureto cool to ambient temperature
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-83bcaef4a189467a84016dd259967098
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…