Methyl iodide → 1-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494171Notes

Reaction equation

HRID 494171 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:14][N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2525137-Nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 114809551-Methyl-7-nitro-1,2,3,4-tetrahydroquinolineYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (7.03 g, 39.4 mmol) in dimethylformamide (50 ml) was added potassium carbonate (16.3 g, 118 mmol) and iodomethane (3.7 ml, 59.1 mmol) and the reaction stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was taken up in water (400 ml) and extracted into ether (3×200 ml). The combined ether extracts were washed with brine (100 ml), dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 20-40% EtOAc/40-60° C. petroleum ether gave the title compound as an orange solid (5.35 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.42 (dd, 1H), 7.33 (d, 1H), 7.01 (d, 1H), 3.31 (m, 2H), 2.96 (s, 3H), 2.80 (t, 2H), 1.99 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted into ether (3×200 ml)
  3. washThe combined ether extracts were washed with brine (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product which
  7. customwas purified by flash column chromatography
  8. washElution with 20-40% EtOAc/40-60° C. petroleum ether

Sources & evidence

ORD record
ord-b83137af8b8d46f9a825513ad2d1533b
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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