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

HRID 1583378Notes

Reaction equation

HRID 1583378 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 dropwise 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. The reaction mixture is stirred at room temperature for 16 hours.

Workup

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

Sources & evidence

ORD record
ord-dff7686330fd4b7ba0fac4132634bc61
Source dataset
uspto-grants-1985_11
Patent number
US04551474

Reaction notes

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