Sulfuric Acid → HCID 58525572, compound

HRID 1894966Notes

Reaction equation

HRID 1894966 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2.S(=O)(=O)(O)O.[C:20](=O)(O)[O-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:20])=[O:13])=[CH:5]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 589024556-Hydroxyquinoline-3-carboxylic acid

Product 1

HCID 58525572HCID 58525572, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

6-Hydroxyquinoline-3-carboxylic acid (Int-15, 1 g, 5.29 mmol) was suspended in methanol (25 mL) to which sulfuric acid (0.3 mL, 5 mmol) was carefully added. The reaction was heated at 70° C. under an atmosphere of nitrogen for 48 h. The reaction was cooled to room temperature and saturated sodium bicarbonate solution (2 mL) was added. The solvent was removed under reduced pressure and the crude residue was co-evaporated with toluene twice. The dried residue was purified by silica gel chromatography (methylene chloride to 95/5 methylene chloride/methanol gradient) to afford Int-16 (0.89 g, 83%). LC-MS: (FA) ES+ 204; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.23 (d, J=1.7 Hz, 1H), 9.09 (s, 1H), 8.05 (d, J=9.1 Hz, 1H), 7.59 (dd, J=9.1, 2.5 Hz, 1H), 7.50 (d, J=2.5 Hz, 1H), 3.96 (s, 3H).

Workup

  1. additionwas carefully added
  2. temperatureThe reaction was cooled to room temperature
  3. customThe solvent was removed under reduced pressure
  4. customThe dried residue was purified by silica gel chromatography (methylene chloride to 95/5 methylene chloride/methanol gradient)
  5. customto afford Int-16 (0.89 g, 83%)

Sources & evidence

ORD record
ord-425feda5cb5e49e3a71471cc1044c2d5
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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