Hydrochloric Acid → 4-Hydroxy-1-methyl-3-nitro-1,2-dihydroquinolin-2-one

HRID 14355

반응식

HRID 14355 반응식
C(O[C:4](=[O:9])[CH2:5][N+:6]([O-:8])=[O:7])C.[H-].[Na+].[H][H].[CH3:14][N:15]1C(=O)O[C:18](=[O:19])[C:17]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:16]12.Cl>CC(N(C)C)=O>[OH:19][C:18]1[C:17]2[C:16](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]([CH3:14])[C:4](=[O:9])[C:5]=1[N+:6]([O-:8])=[O:7]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 25160N-Methylisatoic anhydrideHCID 69379Ethyl nitroacetateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 546821234-Hydroxy-1-methyl-3-nitro-1,2-dihydroquinolin-2-one수율 27%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
90 °C

실험 절차

A solution of ethylnitroacetate (15.96 g, 120 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 5.28 g, 132 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 (23.38 g, 132 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 7.1 g (27%) of yellow solids. Mp 193° C. 1H NMR (DMSO-d6): δ 3.60 (s, 3H), 7.37 (t, J=7.6 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.77 (t, J=7.5 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H). EIMS m/z 221 (M+1), 243 (M+23). Anal. (C10H8N2O4) 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-f5f4df6862dd4fd2a27a8204c0be1017
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732146B2

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