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

HRID 1638576노트

반응식

HRID 1638576 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fcba40e12c824b599e5dcfd42f8d64c8
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04880815

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