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

HRID 458655

反応式

HRID 458655 の反応式
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]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 25160N-Methylisatoic anhydrideHCID 78201Ethyl methanesulfonylacetateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-54b9c75c2d1c43f2be9202bf2dd769f9
出典データセット
uspto-grants-2007_03
特許番号
US07192961B2

関連ノート

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