Nitric Acid → 7-Nitro-1,2,3,4-tetrahydroquinoline

HRID 2102944Notes

Reaction equation

HRID 2102944 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-])([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=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 944Nitric AcidHCID 11430Potassium CarbonateHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 2525137-Nitro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydoquinoline (6.5 g, 0.049 mol) in conc. Sulfuric acid (118 mL) at 0° C. was added a solution of con. nitric acid (4.9 mL) in conc. Sulfuric acid (12 mL) drop-wise over 3 hours so as to maintain the temperatute <5° C. The reaction mixture was then poured onto crushed ice and neutralized with solid potassium carbonate. The mixture was extracted with EtOAc (2×500 mL), the combined organic extracts were washed with water, dried and concentrated to give the crude product which was purified by column chromatography on silica-gel using EtOAc/hexane as eluent to obtain the title compound as an orange solid.

Workup

  1. additionThe reaction mixture was then poured
  2. customonto crushed ice
  3. extractionThe mixture was extracted with EtOAc (2×500 mL)
  4. washthe combined organic extracts were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product which
  8. customwas purified by column chromatography on silica-gel

Sources & evidence

ORD record
ord-c336313f1bcd43d499997b72e3ae294f
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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