Hydroxyamine hydrochloride → 3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde oxime

HRID 985517ノート

反応式

HRID 985517 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]=O)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1.Cl.[NH2:25][OH:26]>C(O)C.CO.ClCCl>[NH3:1].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]=[N:25][OH:26])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1

参加物

7

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 99441283-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde

生成物 2

HCID 222AmmoniaHCID 1372419663-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde oxime収率 189%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde (0.30 g, 1.0 mmol) and hydroxylamine hydrochloride (0.208 g, 3.0 mmol) were suspended in ethanol (15 ml) then heated at 60° C. for 45 min. The mixture was diluted with 50% methanol in dichloromethane (200 ml) and pre-adsorbed onto silica. Purification by flash column chromatography on silica gel eluting with dichloromethane/methanol/conc. ammonia (95:5:0.5) gave the title compound (297 mg, 94%) as a white foam. Further purification of this material by preparative thin-layer chromatography eluting with dichloromethane/methanol/conc. ammonia (95:5:0.5) gave (E)-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde oxime as a white solid followed by (Z)-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde oxime also as a white solid.

後処理

  1. customPurification by flash column chromatography on silica gel eluting with dichloromethane/methanol/conc

出典と根拠

ORDレコード
ord-419302785f934b5883afbb2c4b92614e
出典データセット
uspto-grants-2005_03
特許番号
US06872731B2

反応ノート

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