3-(Cyanomethyl)pyridine-2-carbonitrile → 6-Amino-8-benzyl-1,7-naphthyridine

HRID 369028Notes

Reaction equation

HRID 369028 reaction equation
[C:1]([C:3]1[C:8]([CH2:9][C:10]#[N:11])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[CH2:12]([Mg]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.O1CCCC1>[NH2:11][C:10]1[CH:9]=[C:8]2[C:3](=[C:1]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:2]=1)[N:4]=[CH:5][CH:6]=[CH:7]2

Participants

5

Reactant 2

HCID 46725983-(Cyanomethyl)pyridine-2-carbonitrileHCID 178419663HCID 178419663, compound

Product 1

HCID 232846456-Amino-8-benzyl-1,7-naphthyridine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-cyano-3-pyridylacetonitrile (2 g, 0.014 mol) in toluene (20 ml) is added benzylmagnesium bromide 8.4 ml, 2N in tetrahydrofuran, 0.17 mol) at ambient temperature. After 1 h the reaction is quenched with a saturated solution of ammonium chloride. The product is extracted with ethyl acetate and the organic layer washed with 2N NaOH and water. The product is purified by flash column chromatography on silica gel (10:3 toluene/acetone) affording the title compound. Mass M+H 236; mp 113-116° C.

Workup

  1. customAfter 1 h the reaction is quenched with a saturated solution of ammonium chloride
  2. extractionThe product is extracted with ethyl acetate
  3. washthe organic layer washed with 2N NaOH and water
  4. customThe product is purified by flash column chromatography on silica gel (10:3 toluene/acetone)

Sources & evidence

ORD record
ord-8b5b8840371746999baa1b1e3589ae07
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Reaction notes

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