Water → 1-Methyl-4-nitro-1H-indazole

HRID 1443199

반응식

HRID 1443199 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].CI.[C:15](=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:15][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[N:7]1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 180574-Nitroindazole

생성물 1

HCID 2802131-Methyl-4-nitro-1H-indazole수율 35.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6.5 g of 4-nitroindazole (Chem. Ber. (1904), 37, 2583), 1.9 ml of methyl iodide and 14.4 g of cesium carbonate in 110 ml of DMF are stirred for 2 hours at 0° C. and then for 12 hours at room temperature. It is added to water and extracted with ethyl acetate. The organic phase is washed with water and brine, dried (Na2SO4) and concentrated by evaporation. The residue is recrystallized from ethyl acetate/hexane. 2.49 g of 1-methyl-4-nitroindazole is obtained. The latter is hydrogenated in 70 ml of THF with 420 mg of palladium on activated carbon under normal pressure with hydrogen. The batch is filtered through diatomaceous earth and completely concentrated by evaporation. 2.1 g of the title compound is obtained.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation
  5. customThe residue is recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-448ff966a4e34c64a3d0687be6454d6e
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659297B2

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