Potassium Nitrate → 7-Nitro-1,2,3,4-tetrahydroquinoline

HRID 1805022Notes

Reaction equation

HRID 1805022 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[N+:11]([O-])([O-:13])=[O:12].[K+].C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[N+:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][CH2:2][NH:1]2)=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 24434Potassium NitrateHCID 694601,2,3,4-TetrahydroquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 2525137-Nitro-1,2,3,4-tetrahydroquinolineYield 25%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 1,2,3,4-tetrahydro-quinoline (20.0 g, 0.15 mol) dissolved in H2SO4 (98%, 150 mL), KNO3 (18.2 g, 0.18 mol) was slowly added at 0° C. The reaction was allowed to warm to room temperature and stirred over night. The mixture was then poured into ice-water and basified with sat. NaHCO3 solution to pH 8. After extraction with CH2Cl2, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (petroleum ether-EtOAc, 10:1) to give 7-nitro-1,2,3,4-tetrahydro-quinoline (6.6 g, 25%).

Workup

  1. extractionAfter extraction with CH2Cl2
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 10:1)

Sources & evidence

ORD record
ord-4f5919ab6f6c434ba9233b8e805d5171
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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