Methyl iodide → HCID 15053153, compound

HRID 1088793Notes

Reaction equation

HRID 1088793 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][C:8]12[O:16][CH2:15][CH2:14][O:13]1.[CH2:17]([Li])CCC.CI>O1CCCC1>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]([CH3:17])[CH2:10][CH2:9][C:8]12[O:16][CH2:15][CH2:14][O:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14685734HCID 14685734, compoundHCID 178418339Butyllithium

Product 1

HCID 15053153HCID 15053153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-hydroxymethyl-4,4-ethylenedioxy1,2,3,4-tetrahydroquinoline (2.5 g) in tetrahydrofuran (30 ml) was added n-butyllithium (14.5 to 17% solution in n-hexane) (10 ml) at --40° C. and stirred for 30 minutes. Then methyl iodide (1.9 g) was added to the reaction mixture and the mixture was stirred for 3 hours at -30° C. to -10° C. and for 30 minutes at -5° C. After distilling off the solvent, n-hexane-ethyl acetate was added to the resulting residue and the insoluble matter was filtered off. The filtrate was concentrated to give 8-hydroxymethyl-4,4-ethylenedioxy-1-methyl-1,2,3,4-tetrahydroquinoline (1.9 g).

Workup

  1. stirringthe mixture was stirred for 3 hours at -30° C. to -10° C. and for 30 minutes at -5° C
  2. distillationAfter distilling off the solvent, n-hexane-ethyl acetate
  3. additionwas added to the resulting residue
  4. filtrationthe insoluble matter was filtered off
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e460008f99da4d8bbf4bd5a1527cb529
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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