Acetic Acid → Methyl((quinolin-3-yl)methyl)amine

HRID 18293

反応式

HRID 18293 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.CN.CO.CC(O)=O.[BH3-][C:22]#[N:23].[Na+]>CO>[CH3:22][NH:23][CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 836413-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57454252Monomethylamine methanol

生成物 1

HCID 16494781Methyl((quinolin-3-yl)methyl)amine収率 48.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 3-quinolinecarboxaldehyde (1.5 g, 10 mmole), 2.0 M CH3NH2/MeOH (10 mL, 20 mmole), glacial AcOH (0.6 mL, 10 mmole), and NaBH3CN (0.35 g, 11 mmole) in MeOH (20 mL) was stirred at RT overnight, then was concentrated in vacuo. The residue was diluted with 5% NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel (10% MeOH/CH2Cl2) gave the title compound (0.83 g, 24%) as a slightly yellow viscous oil: MS (ES) m/e 173 (M+H)+.

後処理

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with 5% NaOH
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-72e0a1d798ad4dd1ba89fbb0b193a327
出典データセット
uspto-grants-2010_06
特許番号
US07741339B2

関連ノート

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