4-Fluoro-3-methoxybenzonitrile → 4-Fluoro-3-methoxybenzylamine

HRID 737015노트

반응식

HRID 737015 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].[H][H]>[Pd].C(O)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[O:10][CH3:11]

참가 물질

5

반응물 2

HCID 27373654-Fluoro-3-methoxybenzonitrileHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 442031244-Fluoro-3-methoxybenzylamine수율 134%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

Add 4-fluoro-3-methoxy-benzonitrile (2 g, 0.01 mol), 10% palladium on carbon (0.400 g) and glacial acetic acid (120 ml) to a pressure vessel. Purge the reaction vessel with nitrogen, purge the reaction vessel with hydrogen, pressurize the reaction mixture with hydrogen (415 Kpa), seal the vessel, and agitate the reaction. After 8 hours stop the agitation, vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the 5% palladium on carbon and return the filtrate for product isolation. Concentrate the crude solution, re-dissolve in CH2Cl2 (80 mL) and washe with 5N NaOH (35 mL). Separate the organic and aqueous phases and extract the aqueous with additional CH2Cl2 (20 mL). Combine the organic solutions, dry, filter and concentrate to give the crude material 2.08 g (100%). The title compound as the major product (Rf=0.12, 10% MeOH/CH2Cl2) is used without further purification. MS (ES+) 156.1 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 7.01 (dd, 1H, J=8.2, 11.4), 6.95 (dd, 1H, J=2.1, 8.4), 6.80 (m, 1H), 3.89 (s, 3H), 3.82 (s, 2H), 1.54 (br s, 2H).

후처리

  1. customPurge the reaction vessel with nitrogen
  2. custompurge the reaction vessel with hydrogen
  3. customseal the vessel
  4. customthe reaction
  5. custompurge the vessel with nitrogen
  6. filtrationFilter the reaction mixture
  7. customto remove the 5% palladium on carbon
  8. concentrationConcentrate the crude solution
  9. dissolutionre-dissolve in CH2Cl2 (80 mL)
  10. customSeparate the organic and aqueous phases
  11. extractionextract the aqueous with additional CH2Cl2 (20 mL)
  12. customCombine the organic solutions, dry
  13. filtrationfilter
  14. concentrationconcentrate

출처 및 근거

ORD 기록
ord-eede7645daf948e0b5d15cf79e58ebc7
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595339B2

반응 노트

불러오는 중…