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

HRID 657771

반응식

HRID 657771 반응식
[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

참가 물질

4

반응물 1

HCID 598406937-(Azidomethyl)quinoline

생성물 1

HCID 17904490Quinolin-7-ylmethanamine수율 98.7%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-12c48e6fd3ec4232afc27eb37e2f6f68
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076345B2

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