Methyl iodide → (1-Methyl-1,2,3,4-tetrahydroquinolin-8-yl)methanol

HRID 1088787Notes

Reaction equation

HRID 1088787 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][CH2:10][CH2:9][CH2:8]2.[H-].[Na+].[CH2:15]([Li])CCC.CI>O1CCCC1>[CH3:15][N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:2][OH:1])[CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14072927(1,2,3,4-Tetrahydroquinolin-8-yl)methanolHCID 178418339Butyllithium

Product 1

HCID 15053143(1-Methyl-1,2,3,4-tetrahydroquinolin-8-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 8-hydroxymethyl-1,2,3,4-tetrahydroquinoline (8.03 g) and sodium hydride (60% in oil) (1.97 g) was added tetrahydrofuran (100 ml) under ice-cooling and argon atmosphere, and the mixture was stirred for 2 hours at 70° to 75° C. At -70° C., n-butyllithium (20 ml) was added to the reaction mixture by use of a syringe, and 30 minutes after addition, a solution of methyl iodide (6.98 g) in tetrahydrofuran (30 ml) was added thereto, and the mixture was stirred for 20 hours at room temperature. After distilling off tetrahydrofuran, the resulting residue was extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (4:1)]to give 1-methyl-8-hydroxymethyl-1,2,3,4-tetrahydroquinoline (5.00 g).

Workup

  1. temperaturecooling
  2. addition30 minutes after addition
  3. stirringthe mixture was stirred for 20 hours at room temperature
  4. distillationAfter distilling off tetrahydrofuran
  5. extractionthe resulting residue was extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe resulting residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-78fb6607072844dda15dd6097e758e5d
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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