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

HRID 649201Notes

Reaction equation

HRID 649201 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Br)C1C=CC=CC=1.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>CCOCC>[C:1]1([CH:18]2[CH2:19][CH2:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:17]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7047QuinolineHCID 178419663HCID 178419663, compoundHCID 178506676HCID 178506676, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

By the 3-step method of Preparation E, substituting 1M phenyllithium in ether for the benzylmagnesium bromide solution, quinoline (25 g, 0.194 mol) was converted to present title product, 22.4 g, as an oil.

Workup

  1. customBy the 3-step method of Preparation E

Sources & evidence

ORD record
ord-14a187deddf0425e914ed4619b3b5fe1
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Reaction notes

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