Benzene → 2-Methoxy-5,6,7,8-tetrahydroquinoline

HRID 1106575Notes

Reaction equation

HRID 1106575 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]1=[O:11].[CH:12]1C=CC=CC=1.CI.CCCCCC.C(OCC)(=O)C>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH3:12][O:11][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 6328Methyl iodideHCID 2641061,2,5,6,7,8-Hexahydroquinolin-2-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 181802832-Methoxy-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5,6,7,8-tetrahydro-2-quinolone [Meyers, A. I. and Garcia-Munoz, G., J. Org. Chem. (1964) 29, 1435] (7.20 g, 48.32 mmol) and silver carbonate (9.33 g, 33.82 mmol) in THF (100 ml)-benzene (20 ml) was treated with methyl iodide (4.67 ml, 10.28 g, 72.48 mmol) and then heated at reflux for 18 h. On cooling to room temperature the mixture was filtered and the filtrate concentrated to give a brown oil which was subjected to column chromatography (silica, hexane-ethyl acetate, 2:1) to afford the title compound (4.40 g) as yellow oil MS (ES+) 164 (MH+). δH (CDCl3) 7,23 (1H, d, J 8.3 Hz), 6.47 (1H, d, J 8.3 Hz), 3.88 (3H, s), 2.78 (2H, t, J 5.9 Hz), 2.65 (2H, t, J 5.9 Hz) and 1.88-1.71 (4H, m).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. filtrationwas filtered
  4. concentrationthe filtrate concentrated
  5. customto give a brown oil which

Sources & evidence

ORD record
ord-e1e20ad68861462aa4df92e9f8c78d69
Source dataset
uspto-grants-2000_05
Patent number
US06057329

Reaction notes

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