Sodium Bicarbonate → 8-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl ester

HRID 1529589Notes

Reaction equation

HRID 1529589 reaction equation
C(O[C:4](=[O:22])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[Br:21])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:22])[C:18]2[C:13](=[C:14]([Br:21])[CH:15]=[CH:16][C:17]=2[O:19][CH3:20])[NH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 103846312-[(2-Bromo-5-methoxyphenylamino)methylene]malonic acid diethyl ester

Product 1

HCID 102458028-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[(2-Bromo-5-methoxy-phenylamino)-methylene]-malonic acid diethyl ester (9 g, 24.2 mmol) was slowly added to polyphosphoric acid (30 g) at 120° C. The mixture was stirred at this temperature for additional 30 min and then cooled to room temperature. Absolute ethanol (30 mL) was added and the resulting mixture was refluxed for 30 min. The mixture was basified with aqueous sodium bicarbonate at 25° C. and extracted with EtOAc (4×100 mL). The organic layers were combined, dried and the solvent evaporated to give 8-bromo-5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (2.3 g, 30%).

Workup

  1. temperaturethe resulting mixture was refluxed for 30 min
  2. extractionextracted with EtOAc (4×100 mL)
  3. customdried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-ed6827de2b5e40a290c1d7c8220524e7
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

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