Acetic Acid → HCID 58154530、化合物

HRID 2359400ノート

反応式

HRID 2359400 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][CH2:19][C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 103713-PyridinecarboxaldehydeHCID 3465192-Chloroquinolin-8-amineHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 58154530HCID 58154530、化合物収率 80%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 2-chloroquinolin-8-amine (1.75 g, 9.8 mmol), 3-pyridinecarbaldehyde (2.14 g, 20 mmol) and AcOH (1.2 g, 20 mmol) in MeOH (10 mL) were added NaCNBH3 (1.26 g, 20 mmol) in portions at room temperature, then the reaction mixture was stirred at room temperature for 5 h. The reaction was concentrated in vacuo, and the residue was taken up in CH2Cl2. The solution was washed with water (1×50 mL), dried over Na2SO4, concentrated and purified by silica gel column (20:1 pentane/ethyl acetate) to give 2-chloro-N-(pyridin-3-ylmethyl)quinolin-8-amine as a yellow oil (2.1 g, yield 80%).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. washThe solution was washed with water (1×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column (20:1 pentane/ethyl acetate)

出典と根拠

ORDレコード
ord-569de94d215547e6b79f80d86f08beed
出典データセット
uspto-grants-2014_04
特許番号
US08685970B2

反応ノート

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