Water → 6-Bromo-2-(2-furanyl)-4-quinolinecarboxylic acid

HRID 2170901Notes

Reaction equation

HRID 2170901 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[C:13]([C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH3:14].[OH-:21].[Na+].O>C(O)C.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:13]([C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)[CH:14]=[C:5]2[C:6]([OH:11])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 68895-BromoisatinHCID 145052-AcetylfuranHCID 14798Sodium Hydroxide

Product 1

HCID 6861526-Bromo-2-(2-furanyl)-4-quinolinecarboxylic acidYield 71.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a 500 ml three necked round bottom flask was added 5-bromoisatin (20 g) and 2-acetyl-furan (9.7 g) in ethanol (150 ml) followed by NaOH (9.2 g) in one lot and the resulting brown solution was allowed to stir at RT for 5 minutes. To the above reaction mixture was added water (5 ml) at RT and the reaction mixture was heated to reflux for 2 hours. The completion of the reaction was monitored on TLC using MDC:MeOH (9:1) as a mobile phase. After completion of the reaction, the reaction mixture was filtered hot and water (150 ml) was added to filtrate. The filtrate was then acidified with 5N HCl to pH 6.0-6.5 and the precipitate formed was filtered and washed with water (3*50 ml) followed by ethanol (2*10 ml) to yield 6-bromo-2-(furan-2-yl)quinoline-4-carboxylic acid (20 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered hot
  5. additionwater (150 ml) was added to filtrate
  6. customthe precipitate formed
  7. filtrationwas filtered
  8. washwashed with water (3*50 ml)

Sources & evidence

ORD record
ord-aa8211a8fb744884a430efe2ca227189
Source dataset
uspto-grants-2015_06
Patent number
US09051305B2

Reaction notes

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