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

HRID 6691

반응식

HRID 6691 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-157b7894b4f7449aa2714755436d2131
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084141B2

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