Hydrochloric Acid → 7-(Methylsulfonyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic Acid

HRID 2233393Notes

Reaction equation

HRID 2233393 reaction equation
[C:1](=O)(O)[O-].[Na+].[S:6]([O-:9])([O-])=[O:7].[Na+].[Na+].[O:12]=[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23]([OH:25])=[O:24])=[CH:15][NH:14]1.Cl>O>[CH3:1][S:6]([C:20]1[CH:21]=[C:22]2[C:17]([C:16]([C:23]([OH:25])=[O:24])=[CH:15][NH:14][C:13]2=[O:12])=[CH:18][CH:19]=1)(=[O:9])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 6431611-Oxo-1,2-dihydroisoquinoline-4-carboxylic acid

Product 1

HCID 592959277-(Methylsulfonyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic AcidYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of sodium bicarbonate (500 mg) and sodium sulfite (353 mg) in 4 ml of water at 0° C. was added portionwise the 7-chlorosulfonyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid (see Preparation 16) (400 mg). The reaction was warmed to room temperature and then heated at 80° C. for 2 h. The reaction was cooled to 0° C. and acidified to pH-1 with concentrated hydrochloric acid. The suspension was diluted with 4 ml of water and stirred for 15 minutes at 0° C. then filtered under nitrogen. The solid was washed twice with water and was added to a degassed aqueous solution (3 ml) of potassium hydrogen carbonate (280 mg) at 45° C. Ethanol was then slowly added until the solution became slightly cloudy. Iodomethane (262 μl) was then added and the reaction refluxed (45-50° C.) for 5 h. The reaction was concentrated under vacuum, extracted with ethyl acetate and the aqueous phase acidified with concentrated hydrochloric acid. The reaction was stirred at 0° C. for 30 min. and the solid collected by filtration then recrystalised from acetone to yield the title compound as a white solid (325 mg).

Workup

  1. temperatureheated at 80° C. for 2 h
  2. temperatureThe reaction was cooled to 0° C.
  3. filtrationthen filtered under nitrogen
  4. washThe solid was washed twice with water
  5. additionwas added to a degassed aqueous solution (3 ml) of potassium hydrogen carbonate (280 mg) at 45° C
  6. additionEthanol was then slowly added until the solution
  7. additionIodomethane (262 μl) was then added
  8. temperaturethe reaction refluxed (45-50° C.) for 5 h
  9. concentrationThe reaction was concentrated under vacuum
  10. extractionextracted with ethyl acetate
  11. stirringThe reaction was stirred at 0° C. for 30 min.
  12. filtrationthe solid collected by filtration
  13. customthen recrystalised from acetone

Sources & evidence

ORD record
ord-2da3cece2d39400f9478d6ab55d453dc
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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