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

HRID 970646Notes

Reaction equation

HRID 970646 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 temperature <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-4d04045a6e6a40fd8a3a9194aeae15b2
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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