Sulfuric Acid → 6-(trifluoromethyl)-1H-indazol-5-amine

HRID 1360837ノート

反応式

HRID 1360837 の反応式
[N+]([O-])([O-])=O.[Na+].[F:6][C:7]([F:18])([F:17])[C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[N:13][NH:14]2)=[CH:10][CH:9]=1.S(=O)(=O)(O)O.O.[NH3:25]>>[NH2:25][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:8]=1[C:7]([F:6])([F:17])[F:18])[NH:14][N:13]=[CH:12]2

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 12896473Azane;hydrateHCID 214555996-(trifluoromethyl)-1H-indazole

生成物 1

HCID 579513676-(trifluoromethyl)-1H-indazol-5-amine収率 94%

実験手順

Under ice-cooling, 1.01 g (12.0 mmol) of sodium nitrate was added to a mixture of 1.54 g (8.29 mmol) of 6-trifluoromethylindazole and 5 ml of concentrated sulfuric acid, and the mixture was stirred for 1 hour. The reaction mixture was poured onto ice and after ammonia water was added dropwise to the mixture under ice-cooling until pH reached 10 or higher, the precipitated solid was collected by filtration and then washed with water, followed by drying. The resulting crude product was dissolved in 50 ml of methanol, activated carbon was added to the mixture, and the mixture was filtered. 0.20 g of 5% Palladium-on-carbon was added to the filtrate, and the mixture was stirred under a hydrogen atmosphere at room temperature for 14 hours. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to give 1.57 g (yield: 94%, two steps) of 5-amino-6-trifluoromethylindazole.

後処理

  1. temperatureUnder ice-cooling
  2. additionThe reaction mixture was poured onto ice
  3. temperaturecooling until pH
  4. filtrationhigher, the precipitated solid was collected by filtration
  5. washwashed with water
  6. customby drying
  7. dissolutionThe resulting crude product was dissolved in 50 ml of methanol
  8. additionactivated carbon was added to the mixture
  9. filtrationthe mixture was filtered
  10. addition0.20 g of 5% Palladium-on-carbon was added to the filtrate
  11. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 14 hours
  12. filtrationThe mixture was filtered through Celite
  13. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-fe4bce7044bb4b86bfea569bdf17a5e4
出典データセット
uspto-grants-2011_02
特許番号
US07879887B2

反応ノート

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