Ethanol → 8-Bromo-2-methylquinoline-4-carboxylic Acid Ethyl Ester

HRID 47434Notes

Reaction equation

HRID 47434 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:21]([O:14][C:13]([C:7]1[C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([CH3:12])[CH:8]=1)=[O:15])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 40398258-Bromo-2-methylquinoline-4-carboxylic acid

Product 1

HCID 698313558-Bromo-2-methylquinoline-4-carboxylic Acid Ethyl Ester

Procedure

A stirred mixture of 8-bromo-2-methylquinoline4-carboxylic acid (7.2 g), ethanol (150 ml) and conc. sulfuric acid (3 ml) was boiled for 6 h. After cooling to room temperature solvent was removed at reduced pressure, the residue treated with water and neutralised with solid potassium carbonate. The neutralised mixture was extracted with ethyl acetate, the extracts dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel (30% diethyl ether/60-80 petroleum ether) to give the ester (2.5 g). m/z (API+): 294, 296 (MH+).

Workup

  1. customwas removed at reduced pressure
  2. additionthe residue treated with water and neutralised with solid potassium carbonate
  3. extractionThe neutralised mixture was extracted with ethyl acetate
  4. dry with materialthe extracts dried (MgSO4) and solvent
  5. customremoved at reduced pressure
  6. customchromatographed (silica gel (30% diethyl ether/60-80 petroleum ether)

Sources & evidence

ORD record
ord-69c412652c2841b79b5736ea77e64829
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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