Ethyl Acetate → HCID 19592716, compound

HRID 613580Notes

Reaction equation

HRID 613580 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=[O:26])[C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([O:22]C)[C:15]=1[O:24]C.B(Br)(Br)Br.C(OCC)(=O)C>ClCCl.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=[O:26])[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:22])[C:15]=1[OH:24]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 19592875HCID 19592875, compound

Product 1

HCID 19592716HCID 19592716, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-bromo-8-(2,3,4-trimethoxybenzoylamino)quinoline (700 mg) in dichloromethane (10 ml) was added 1M solution of boron tribromide in dichloromethane (5.5 ml) under ice-cooling, and the mixture was stirred for 2 hours at ambient temperature. To the mixture was added ice-water, and the mixture was stirred for 1.5 hours. The mixture was adjusted to pH 4 with IN sodium hydroxide solution, and ethyl acetate was added thereto. The mixture was stirred at ambient temperature overnight, and the insoluble material was filtered off. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (methanol-dichloromethane) to give 3-bromo-8-(2,3,4-trihydroxybenzoylamino)quinoline (110 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.5 hours
  3. additionwas added
  4. stirringThe mixture was stirred at ambient temperature overnight
  5. filtrationthe insoluble material was filtered off
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography (methanol-dichloromethane)

Sources & evidence

ORD record
ord-a74f1f53fafb40adab7724a416dd9dde
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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