Hydrochloric Acid → 4-Hydroxy-3-methanesulfonyl-1-methyl-1H-quinolin-2-one

HRID 458566

Reaction equation

HRID 458566 reaction equation
C(O[C:4](=[O:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])C.[H-].[Na+].[H][H].[CH3:15][N:16]1C(=O)O[C:19](=[O:20])[C:18]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:17]12.Cl>CC(N(C)C)=O>[OH:20][C:19]1[C:18]2[C:17](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:16]([CH3:15])[C:4](=[O:10])[C:5]=1[S:6]([CH3:9])(=[O:7])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 25160N-Methylisatoic anhydrideHCID 78201Ethyl methanesulfonylacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 546805794-Hydroxy-3-methanesulfonyl-1-methyl-1H-quinolin-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of ethylmethanesulfonylacetate (3.78 g, 22.74 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 1.07 g, 25 mmol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min and cooled to room temperature. A solution of N-methylisatoic anhydride (4.43 g, 25 mmol) in dimethylacetamide was added slowly and heated overnight at 120° C. The mixture was cooled to room temperature, poured into ice water and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 2.76 g (48%) of white solids. Mp 170° C. 1H NMR (DMSO-d6): δ 3.51 (s, 3H), 3.59 (s, 3H), 7.39 (t, J=7.4 Hz, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.84 (t, J=7.0 Hz, 1H), 8.09 (d, J=8.0 Hz, 1H). EIMS m/z 254 (M+1), 276 (M+23). Anal. (C11H11NO4S) C, H, N.

Workup

  1. temperaturecooled to room temperature
  2. temperatureheated overnight at 120° C
  3. temperatureThe mixture was cooled to room temperature
  4. customThe solids formed
  5. filtrationwere filtered
  6. washwashed several times by water

Sources & evidence

ORD record
ord-a01bf483957a4d1e9b9fd1e7a365f1e1
Source dataset
uspto-grants-2007_03
Patent number
US07192955B2

Linked notes

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