Water → 4-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline-N-oxide

HRID 649170Notes

Reaction equation

HRID 649170 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-:15])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[N+]([O-])=O.[OH-].[Na+].O.[CH2:19]([OH:22])[CH:20]=[CH2:21]>>[CH2:19]([O:22][C:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N+:4]([O-:15])=[CH:3][C:2]=1[CH3:1])[CH:20]=[CH2:21]

Participants

5

Reactant 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 14798Sodium HydroxideHCID 139602613-methyl-4-nitro-5,6,7,8-tetrahydroquinoline-N-oxide

Product 1

HCID 141555204-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline-N-oxide

Procedure

2.0 Grams of 3-methyl-4-nitro-5,6,7,8-tetrahydroquinoline-N-oxide was dissolved in allyl alcohol. Then 0.6 g of sodium hydroxide was added thereto, and the mixture was stirred at 70°-80° C. for 3 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure, to the residue thus obtained was added water, and was 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 under reduced pressure to obtain 1.4 g of 4-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline-N-oxide in the form of brown oily substance.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure, to the residue
  2. customthus obtained
  3. extractionwas extracted with chloroform
  4. washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customChloroform was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b996dfc1b23e4740bdd6961c6e3ae78d
Source dataset
uspto-grants-1988_04
Patent number
US04738970

Reaction notes

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