Nitric Acid → 6-Fluoro-2-methyl-5-nitroquinoline

HRID 637435

反応式

HRID 637435 の反応式
S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]2.[N:18]([O-:20])=[O:19].[Na+].[N+]([O-])(O)=O.[OH-].[NH4+]>>[F:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]2

参加物

6

反応物 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 707846-Fluoro-2-methylquinolineHCID 23668193Sodium Nitrite

生成物 1

HCID 27483306-Fluoro-2-methyl-5-nitroquinoline

反応条件

温度
20 °C

実験手順

To 3.5 l of fuming sulfuric acid were added, with cooling, 600 g (3.73 moles) of 6-fluoroquinaldine in small portions (5 to 10 g). To this mixture was added about 0.1 g of sodium nitrite, followed by the dropwise addition of 261 ml of fuming red nitric acid over a period of six hours. The temperature of the mixture was maintained at 5° to 10° C. during the addition. The mixture was stirred at 20° C. for sixteen hours, then poured into 3 gallons of ice. Ammonium hydroxide was added, with cooling, to basify the mixture. The precipitated solid was separated by filtration, and dissolved in about two liters of warm toluene. The solution was dried over magnesium sulfate, filtered and evaporated to provide a yellow solid (6-fluoro-5-nitroquinaldine, m.p. 105°-108° C.) which was recrystallized from 1,2dicholoroethane. The structural assignment was confirmed by nuclear magnetic resonance and infrared spectral analyses.

後処理

  1. temperaturewith cooling
  2. temperatureThe temperature of the mixture was maintained at 5° to 10° C. during the addition
  3. temperaturewith cooling
  4. customThe precipitated solid was separated by filtration
  5. dissolutiondissolved in about two liters of warm toluene
  6. dry with materialThe solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-0b2587d8b1e14eb7b2f82d57518f133d
出典データセット
uspto-grants-1985_12
特許番号
US04556713

関連ノート

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