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

HRID 14355

反応式

HRID 14355 の反応式
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]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 25160N-Methylisatoic anhydrideHCID 69379Ethyl nitroacetateHCID 178418361HCID 178418361、化合物

生成物 1

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

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 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.

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-f5f4df6862dd4fd2a27a8204c0be1017
出典データセット
uspto-grants-2010_06
特許番号
US07732146B2

関連ノート

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