Nitric Acid → 3-methyl-4-nitro-5,6,7,8-tetrahydroquinoline-N-oxide

HRID 649169ノート

反応式

HRID 649169 の反応式
[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[N+:13]([O-])([OH:15])=[O:14].S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[N+:13]([O-:15])=[O:14]

参加物

5

反応物 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 123582463-Methyl-1-oxo-5,6,7,8-tetrahydro-1lambda~5~-quinoline

生成物 1

HCID 139602613-methyl-4-nitro-5,6,7,8-tetrahydroquinoline-N-oxide

実験手順

6.5 Grams of 3-methyl-5,6,7,8-tetrahydroquinoline-N-oxide was added dropwise in a mixture consisting of 7 ml of fuming nitric acid and 7 ml of concentrated sulfuric acid under ice-cooled condition with stirring. The reaction mixture was stirred at 40° C. for 2 hours, then further stirred at 60° C. for 2 hours. The reaction mixture was poured in a cold aqueous solution of sodium hydroxide, then extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate. Chloroform was removed by evaporation, and the thus obtained residue was recrystallized from ethyl acetate-ethanol-n-hexane to yield 5.3 g of 3-methyl-4-nitro-5,6,7,8-tetrahydroquinoline-N-oxide.

後処理

  1. temperaturecooled condition
  2. stirringThe reaction mixture was stirred at 40° C. for 2 hours
  3. stirringfurther stirred at 60° C. for 2 hours
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customChloroform was removed by evaporation
  8. customthe thus obtained residue was recrystallized from ethyl acetate-ethanol-n-hexane

出典と根拠

ORDレコード
ord-9aeb4166a4d2413e9d216d9e760cb6b7
出典データセット
uspto-grants-1988_04
特許番号
US04738970

反応ノート

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