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

HRID 369028

反応式

HRID 369028 の反応式
[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

参加物

5

反応物 2

HCID 46725983-(Cyanomethyl)pyridine-2-carbonitrileHCID 178419663HCID 178419663、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8b5b8840371746999baa1b1e3589ae07
出典データセット
uspto-grants-2000_10
特許番号
US06136821

関連ノート

読み込み中…