Sodium Bicarbonate → HCID 21824645, compound

HRID 505226Notes

Reaction equation

HRID 505226 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](S(O)(=O)=O)[C:5]2[CH:6]=[CH:7][C:8]([CH3:13])=[N:9][C:10]=2[C:11]=1[OH:12].C([O-])(O)=O.[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.O>[Cl:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 21824655HCID 21824655, compound

Product 1

HCID 21824645HCID 21824645, compoundYield 82.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

7-Chloro-8-hydroxy-2-methyl-quinoline-5-sulfonic acid (5.50 g, 20.09 mmol) was dissolved in acetic acid (30 ml) and sulfuric acid (3 ml), and the resulting solution was heated to 130° C. for 72 hours. Upon cooling, the reaction mixture was diluted with water (300 ml) and neutralized by the addition of solid NaHCO3. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (gradient of hexane/EtOAc 95:5 to 70:30) to afford the title compound (3.20 g, 82%) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): δ=10.6-10.1 (br, 1H), 8.30 (d, J=7.7 Hz, 1H), 7.55-7.51 (m, 2H), 7.43 (d, J=8.8 Hz, 1H), 2.77 (s, 3H). MS (ES−): 192.2 (M−H)−.

Workup

  1. temperatureUpon cooling
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash chromatography (gradient of hexane/EtOAc 95:5 to 70:30)

Sources & evidence

ORD record
ord-5c64b891e7294efbab0e28a44218a317
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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