3-Pyridinemethanol → 2-(Pyridin-3-yloxy)acetonitrile

HRID 1090241Notes

Reaction equation

HRID 1090241 reaction equation
N1C=CC=C(C[O:8][CH2:9][CH2:10][NH2:11])C=1.[Na].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](CO)[CH:14]=1.ClCC#N>CN(C)C=O>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:8][CH2:9][C:10]#[N:11])[CH:14]=1

Participants

6

Reactant 4

HCID 75103-PyridinemethanolHCID 7856ChloroacetonitrileHCID 5360545SodiumHCID 14547293HCID 14547293, compound

Product 1

HCID 199146182-(Pyridin-3-yloxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting amine, (3-pyridinyl)methyloxyethylamine, was prepared by the following procedure: reaction of the sodium salt of 3-pyridinylmethanol and chloracetonitrile in dimethylformamide gave 2-(3-pyridinyloxy)acetonitrile, which, upon reduction with borane in tetrahydroduran solution, gave the desired amine.

Sources & evidence

ORD record
ord-f651c32dc42d41d5956b9b9d5d8f681f
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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