4-Fluorobenzonitrile → 4-(p-Cyanophenoxy)-2-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1632835Notes

Reaction equation

HRID 1632835 reaction equation
[CH3:1][N:2]1[CH2:11][CH:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[H-].[Na+].F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>CN(C=O)C>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([O:12][CH:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][N:2]([CH3:1])[CH2:11]2)=[CH:17][CH:18]=1)#[N:21]

Participants

5

Reactant 3

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 125230552-Methyl-1,2,3,4-tetrahydro-4-isoquinolinol

Product 1

HCID 131170924-(p-Cyanophenoxy)-2-methyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1,2,3,4-tetrahydro-2-methyl-4-isoquinolinol (3.0 g, 0.018 mole) in dry DMF (15 ml) is added dropwsie under nitrogen to a suspension of sodium hydride 50% (98%) (1.1 g, 0.022 mole), previously washed with hexane, in dry DMF (25 ml). The mixture is warmed to 60° C., at which time a solution of 4-fluorobenzonitrile (2.2 g, 0.018 mole) in dry DMF (15 ml) is slowly added.

Workup

  1. washpreviously washed with hexane, in dry DMF (25 ml)
  2. additionis slowly added

Sources & evidence

ORD record
ord-4ac95f8e80364a5998df9c8cf295e27d
Source dataset
uspto-grants-1984_10
Patent number
US04477670

Reaction notes

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