Trifluoroacetic acid → 5-(3-Amino-benzyl)-1,3-dihydro-indol-2-one

HRID 640980

반응식

HRID 640980 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)=O)([O-])=O.C(O)(C(F)(F)F)=O>[Pd].CN(C=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 686984765-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one

생성물 1

HCID 686962255-(3-Amino-benzyl)-1,3-dihydro-indol-2-one수율 69.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매

실험 절차

The PARR apparatus was charged with was charged with 5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one (50 g, 0.18 mol), 10% Pd/C (5 g) and DMF (500 mL). The reactor was evacuated, purged with N2(g) then filled with H2(g) (60 psi) at room temperature. After hydrogenating at 60 psi for 45 min thin layer choromatographic analysis (TLC) (Hexanes/EtOAc 1:1) indicated that the reaction had caused the reduction of the nitro group to an amine and the reduction of the keto group to the alcohol. Subsequently, TFA 926 mL, 0.35 mol) was added and the reaction was continued for 4 h. The reaction was filtered though celite and the solvet from the filtrate was removed in vacuo. The solids obtained were washed with saturated NaHCO3(aq) (500 mL), and H2O (500 mL) then triturated with Metyl Ether (500 mL) and then triturated again with methanol to afford 5-(3-Amino-benzyl)-1,3-dihydro-indol-2-one (30 g, 67%).

후처리

  1. additionThe PARR apparatus was charged
  2. customThe reactor was evacuated
  3. custompurged with N2(g)
  4. additionthen filled with H2(g) (60 psi) at room temperature
  5. waitthe reaction was continued for 4 h
  6. filtrationThe reaction was filtered though celite
  7. customthe solvet from the filtrate was removed in vacuo
  8. customThe solids obtained
  9. washwere washed with saturated NaHCO3(aq) (500 mL), and H2O (500 mL)
  10. customthen triturated with Metyl Ether (500 mL)
  11. customtriturated again with methanol

출처 및 근거

ORD 기록
ord-45b389062e70437b87f4d2ccd6622be7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

연결된 노트

불러오는 중…