Methyl iodide → HCID 53865664, compound

HRID 1764691Notes

Reaction equation

HRID 1764691 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[CH:13]([C:17]#[N:18])[CH2:12][CH2:11][CH2:10][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:21]I>O1CCCC1>[CH3:21][C:13]1([C:17]#[N:18])[CH2:12][CH2:11][CH2:10][C:9]2[N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:16]=[CH:15][C:14]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12519873HCID 12519873, compound

Product 1

HCID 53865664HCID 53865664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.7 g. of 2-phenyl-5,6,7,8-tetrahydro-5-quinoline carbonitrile in 80 ml. of absolute tetrahydrofuran is combined with 0.660 g. of 80% sodium hydride, agitated for 30 minutes at room temperature and for 30 minutes at 60° C. under nitrogen, and combined with 2.5 ml. of methyl iodide. After heating the mixture for 2 hours to 60° C., it is concentrated, distributed between ethyl acetate/water, and the ethyl acetate phase is concentrated. Recrystallization from diisopropyl ether/hexane yields 5-methyl-2-phenyl-5,6,7,8-tetrahydro-5-quinoline carbonitrile, m.p. 114.5° - 115.5° C.

Workup

  1. temperatureAfter heating the mixture for 2 hours to 60° C., it
  2. concentrationis concentrated
  3. concentrationthe ethyl acetate phase is concentrated
  4. customRecrystallization from diisopropyl ether/hexane

Sources & evidence

ORD record
ord-68f21f2b5bb5499ab1a9550a56fc0c2b
Source dataset
uspto-grants-1978_09
Patent number
US04117135

Reaction notes

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