Ethanol → 2-Phenyl-1,2,3,4-tetrahydroquinoline

HRID 1062581Notes

Reaction equation

HRID 1062581 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[Na]>O>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 715452-Phenylquinoline2×HCID 5360545Sodium

Product 1

HCID 107529152-Phenyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In Scheme A, step 2, the 2-phenyl-1,2,3,4-tetrahydroquinoline of formula (3) is prepared by reducing 2-phenylquinoline of formula (2). For example, 2-phenylquinoline of formula (2) is dissolved in a suitable alcoholic solvent, such as absolute ethanol. Sodium metal is then added and the reaction is allowed to cool to room temperature. The reaction mixture may then be diluted with water and extracted with a suitable organic solvent, such as methylene chloride, ethyl acetate, or chloroform. The combined extracts may then be washed with water and brine, the organic layer is separated and dried and the solvent is evaporated in vacuo to provide the 2-phenyl-1,2,3,4-tetrahydroquinoline of formula (3) which may be used without further purification.

Workup

  1. customIn Scheme A, step 2, the 2-phenyl-1,2,3,4-tetrahydroquinoline of formula (3) is prepared
  2. extractionextracted with a suitable organic solvent, such as methylene chloride, ethyl acetate, or chloroform
  3. washThe combined extracts may then be washed with water and brine
  4. customthe organic layer is separated
  5. customdried
  6. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-209114e7ea504d76ac9ea7df8e82e714
Source dataset
uspto-grants-2005_11
Patent number
US06962928B2

Reaction notes

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