Acetic Acid → HCID 22562008, 화합물

HRID 1839618노트

반응식

HRID 1839618 반응식
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.C([OH:24])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn]>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10](=[O:24])[NH:11]2

참가 물질

7

반응물 4

HCID 176Acetic Acid2회HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561889HCID 22561889, 화합물

생성물 1

HCID 22562008HCID 22562008, 화합물수율 74%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6386tert-Butanol용매

실험 절차

To the suspension of 4-bipheny-2-yl-1H-indole (1.18 g, 4.4 mmol) in t-BuOH:ethanol:acetic acid (28 mL:17 mL:9 mL) was added pyridinium tribromide (4.39 g, 13.7 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (22 mL). Zinc dust (1.63 g, 25 mmol) was added to the reaction mixture portionwise. After stirring for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water (3×), sat. NaHCO3, brine, dried over Na2SO4, concentrated and triturated with ether to give 0.93 g (74%) of 4-biphenyl-2-yl-1,3-dihydro-indol-2-one.

후처리

  1. stirringAfter stirring for one hour
  2. filtrationany unreacted zinc was filtered off and most of the solvent
  3. customwas removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water (3×), sat. NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customtriturated with ether

출처 및 근거

ORD 기록
ord-3efc3f1445eb48c4b0e963ca470cb86c
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677368B2

반응 노트

불러오는 중…