2,4-Dimethyl-5-nitroaniline → 5-methyl-6-nitro-1H-indazole

HRID 539633

반응식

HRID 539633 반응식
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH2:4].[N:13]([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:9][C:7]1[CH:8]=[C:2]2[C:3](=[CH:5][C:6]=1[N+:10]([O-:12])=[O:11])[NH:4][N:13]=[CH:1]2

참가 물질

5

반응물 2

HCID 2280072,4-Dimethyl-5-nitroanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 126378375-methyl-6-nitro-1H-indazole수율 58.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

2,4-Dimethyl-5-nitroaniline (1.662 g, 10.00 mmol) was dissolved in glacial acetic acid (100 ml) and the mixture was cooled to 0° C. A solution of sodium nitrite (1 eq, 690 mg) in water (2 ml) was added while maintaining a temperature below 25° C. Stirring was continued for three hours and the mixture was filtered. The filtrate was allowed to stand for three days at room temperature, then was concentrate under reduced pressure. The residue was diluted with water and the resulting mixture was stirred vigorously. The solid product was collected by filtration, washed thoroughly with cold water, and dried. The product was purified by flash chromatography (99:1 dichloromethane/methanol) to give 1.030 g (58.1%) of 5-methyl-6-nitro-1H-indazole as a solid.

후처리

  1. temperaturewhile maintaining a temperature below 25° C
  2. filtrationthe mixture was filtered
  3. waitto stand for three days at room temperature
  4. concentrationwas concentrate under reduced pressure
  5. additionThe residue was diluted with water
  6. stirringthe resulting mixture was stirred vigorously
  7. filtrationThe solid product was collected by filtration
  8. washwashed thoroughly with cold water
  9. customdried
  10. customThe product was purified by flash chromatography (99:1 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-34ca48c223cf48389784a9d964907b2c
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871760B2

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