Methyl iodide → 1,2,3,4-Tetrahydro-1-methylquinoline

HRID 641916

Reaction equation

HRID 641916 reaction equation
[H-].[Na+].[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.I[CH3:14]>O1CCCC1>[CH3:14][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 681091,2,3,4-Tetrahydro-1-methylquinolineYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

NaH (12 g, 60%, 300.00 mmol) was added in several batches, to a solution of 1,2,3,4-tetrahydroquinoline (26.6 g, 199.70 mmol) in tetrahydrofuran (150 mL) at 0-5° C. The resulting solution was maintained at 0-5° C. for 30 minutes, then iodomethane (50 g, 352.11 mmol) was added dropwise (at 0-5° C.). The resulting solution was then stirred at room temperature overnight. The mixture was filtered, and the filtrate was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to afford 19 g (61%) of 1-methyl-1,2,3,4-tetrahydroquinoline as a yellow liquid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by column chromatography

Sources & evidence

ORD record
ord-d054ad27cc39446d909b8aae5977ee47
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Linked notes

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