8-Hydroxy-2-quinolinecarboxaldehyde → HCID 178515865、化合物

HRID 623401

反応式

HRID 623401 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH:26]=O)[CH:22]=[CH:21]2.[NH2:28][CH2:29][CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1>ClC(Cl)C>[NH:33]1[CH:32]=[C:31]([CH2:30][CH2:29][NH:28][CH2:26][C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[C:16]([OH:15])[CH:17]=[CH:18][CH:19]=3)[N:24]=2)[N:35]=[CH:34]1

参加物

5

反応物 3

HCID 5993428-Hydroxy-2-quinolinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178419017HCID 178419017、化合物

生成物 1

HCID 178515865HCID 178515865、化合物収率 61.5%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

Sodium triacetoxyborohydride (225 mg, 1.061 mmol) was added to a stirred solution of 8-hydroxy-quinoline-2-carboxaldehyde 4 (200 mg, 1.156 mmol) and histamine (128 mg, 1.152 mmol) in dichloroethane (10 mL). The mixture was left to stir at RT for 16 h, neutralized (aqueous NaHCO3), and concentrated. The resulting residue, after column chromatography on silica (ethyl acetate/i-PrOH/2 N NH4OH, 6:2:1), afforded 2-{[2-(1H-imidazol-4-yl)-ethylamino]-methyl}-quinolin-8-ol F1 as a straw-colored solid (190 mg, 61%). The above method was repeated using other amines: 2-(aminomethyl)pyridine gave F2 and 2-(2-methylaminoethyl)pyridine gave F3, data given in Table 2.

後処理

  1. waitThe mixture was left
  2. concentrationneutralized (aqueous NaHCO3), and concentrated

出典と根拠

ORDレコード
ord-1f794a459d554cc18dff04c98dac70f1
出典データセット
uspto-grants-2016_04
特許番号
US09302993B2

関連ノート

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