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

HRID 2352912

반응식

HRID 2352912 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 chromatographic 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 through celite and the solvent 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 Methyl-t-Butyl 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 through celite
  7. customthe solvent 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 Methyl-t-Butyl Ether (500 mL)
  11. customtriturated again with methanol

출처 및 근거

ORD 기록
ord-3823155269ee49c087a320dacdf9771f
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749530B2

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