Water → 2-Methyl-1,2,3,4-tetrahydroquinoline

HRID 649203Notes

Reaction equation

HRID 649203 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Na].O>C(O)C>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 70602-MethylquinolineHCID 5360545Sodium

Product 1

HCID 962892-Methyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methylquinoline (10 g, 0.070 mol) was refluxed in 250 ml ethanol. While refluxing, sodium (22.9 g, 1.0 mol) was added cautiously over a period of 1 hour. The mixture was refluxed for an additional 3.5 hours, cooled to room temperature, poured into 500 ml H2O, and extracted 3×500 ml toluene. The organic layers were combined, dried (K2CO3) and stripped to yield title produce as an oil, 9.2 g.

Workup

  1. temperatureWhile refluxing
  2. temperatureThe mixture was refluxed for an additional 3.5 hours
  3. extractionextracted 3×500 ml toluene
  4. dry with materialdried (K2CO3)
  5. customto yield title
  6. customproduce as an oil, 9.2 g

Sources & evidence

ORD record
ord-6041ad17b4a34f658eb207567f98a363
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Reaction notes

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