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

HRID 970647Notes

Reaction equation

HRID 970647 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=O)C>[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-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 7-nitro-1,2,3,4-tetrahydroquinoline (4.5 g, 25.25 mmol) in DMF (50 mL) was added potassium carbonate (15 g) followed by iodomethane (5.54 g, 39.0 mMol) and the mixture was agitated overnight at ambient temperature. The mixture was poured onto water and extracted with ether (3×200 mL). The combined ethereal extracts were washed with brine, dried and concentrated to give the crude product which was purified by column chromatography on silica-gel to obtain the title compound as an orange liquid.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with ether (3×200 mL)
  3. washThe combined ethereal extracts were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by column chromatography on silica-gel

Sources & evidence

ORD record
ord-55631c51fe0445dd835efdad689fbc46
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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