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

HRID 1638577Notes

Reaction equation

HRID 1638577 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-5,6,7,8tetrahydroquinoline-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 magnsium 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 magnsium sulfate
  6. customChloroform was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-22176e2832704fe880ec6c6d19284215
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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