HCID 20682300, 화합물 → HCID 57531883, 화합물

HRID 1455211노트

반응식

HRID 1455211 반응식
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[C:5]([F:11])[CH:4]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 20682300HCID 20682300, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 57531883HCID 57531883, 화합물수율 95%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A solution of 4-ethyl-2-fluoro-benzonitrile (1.19 g, 8.0 mmol) in ether (70 mL) was cooled in an ice bath. To the cold, stirred solution was added LiAlH4 (600 mg, 16 mmol). The suspension was then heated to reflux. After several hours at reflux, the suspension was allowed to cool to ambient temperature and was quenched by the careful addition of H2O (600 μL), followed by 15% aqueous NaOH (600 μL), and finally H2O (1.8 mL). The resulting suspension was filtered, and the solids were washed thoroughly with ether. The filtrate was concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzylamine (1.16 g, 95% yield) as a liquid. This material was used for the subsequent amide formation without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.21 (1H, app t, J=7.6 Hz), 6.96-6.86 (2H, m), 3.85 (2H, s), 2.63 (2H, q, J=7.6 Hz), 1.22 (3H, t, J=7.6 Hz).

후처리

  1. temperatureThe suspension was then heated to reflux
  2. temperatureAfter several hours at reflux
  3. customwas quenched by the careful addition of H2O (600 μL)
  4. filtrationThe resulting suspension was filtered
  5. washthe solids were washed thoroughly with ether
  6. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-366f4ed28d5d4c0e84ebe3e5984e5ac3
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482366B2

반응 노트

불러오는 중…