7-(Azidomethyl)quinoline → Quinolin-7-ylmethanamine

HRID 657771

反応式

HRID 657771 の反応式
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)=[N+]=[N-]>[Ni].CO>[N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([CH2:4][NH2:1])[CH:14]=2)[CH:9]=[CH:10][CH:11]=1

参加物

4

反応物 1

HCID 598406937-(Azidomethyl)quinoline

生成物 1

HCID 17904490Quinolin-7-ylmethanamine収率 98.7%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

7-(Azidomethyl)quinoline (1.1 g, 5.7 mmol) was hydrogenated (1 atm) in the presence of Raney nickel (1.5 g, 26 mmol) in methanol (30 mL) until completion of the reaction. Catalyst was filtered off and the filtrate was concentrated under reduced pressure to a yellow oil which was dissolved in EtOAc (32 mL) and extracted with 1N hydrochloric acid (3×32 mL). The combined acidic aqueous phases were adjust to pH˜10 with 1N sodium hydroxide solution, and extracted with EtOAc (3×35 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford a white solid (0.89 g, 94%).

後処理

  1. customuntil completion of the reaction
  2. filtrationCatalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure to a yellow oil which
  4. dissolutionwas dissolved in EtOAc (32 mL)
  5. extractionextracted with 1N hydrochloric acid (3×32 mL)
  6. extractionextracted with EtOAc (3×35 mL)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-12c48e6fd3ec4232afc27eb37e2f6f68
出典データセット
uspto-grants-2011_12
特許番号
US08076345B2

関連ノート

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