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

HRID 1938411Notes

Reaction equation

HRID 1938411 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]>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

4

Reactant 2

HCID 944Nitric AcidHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 2525137-Nitro-1,2,3,4-tetrahydroquinolineYield 61.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1,2,3,4-Tetrahydroquinoline (5 g, 0.0375 mol) was dissolved in 16 mL of sulfuric acid and the temperature lowered to 0° C., then 90% fuming nitric acid (1.67 mL, 0.0375 mol) was added slowly and the mixture strirred at 0° C. for 30 min. It was then poured onto 100 g of ice and extracted with dichloromethane (2×100 mL). The organic phase was washed with saturated aqueous solution of NaHCO3 (75 mL) and concentrated in vacuo to a reddish residue that was subjected to chromatography (silica gel, hexanes/ethyl acetate, 8:2) which afforded 4.1 g (61%) of 7-nitro-1,2,3,4-tetrahydroquinoline. Data for 7-nitro-1,2,3,4-tetrahydroquinoline: 1H NMR (400 MHz, CDCl3) 7.39 (dd, J=8.3, 2.2, 1H), 7.26 (d, J=3.5, 1H), 7.01 (d, J=8.3, 1H), 4.16 (bs, 1H), 3.35 (t, J=5.0, 2H), 2.8 (t, J=6.3, 2H), 1.95 (quintet, J=6.1, 2H).

Workup

  1. customlowered to 0° C.
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washThe organic phase was washed with saturated aqueous solution of NaHCO3 (75 mL)
  4. concentrationconcentrated in vacuo to a reddish residue that

Sources & evidence

ORD record
ord-b312ebdf902843c482e6d27c1caf15c7
Source dataset
uspto-grants-1997_12
Patent number
US05693646

Reaction notes

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