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

HRID 539633

反応式

HRID 539633 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 126378375-methyl-6-nitro-1H-indazole収率 58.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-34ca48c223cf48389784a9d964907b2c
出典データセット
uspto-grants-2014_10
特許番号
US08871760B2

関連ノート

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