Acetic Acid → HCID 22561914, 화합물

HRID 1839627노트

반응식

HRID 1839627 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([OH:22])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].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14](=[O:22])[NH:15]3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

8

반응물 4

HCID 176Acetic Acid2회HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 225616844-(3,4-dimethoxy-phenyl)1H-indole

생성물 1

HCID 22561914HCID 22561914, 화합물수율 65%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

To the suspension of 4-(3,4-dimethoxy-phenyl)-1H-indole (14.7 g, 58 mmol) in t-BuOH:ethanol:acetic acid (367 mL:217 mL:113 mL) was added pyridinium tribromide (55.68 g, 174 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added more acetic acid (287 mL). Zinc dust (18.95 g, 290 mmol) was added to the reaction mixture portionwise. After stirring for one hour, water was added to the reaction. The 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 (6×), sat. NaHCO3 (2×), brine (3×), dried over Na2SO4, concentrated and triturated with ether to give 10.14 g (65%) of 4-(3,4-dimethoxy-phenyl)-1,3-dihydro-indol-2-one as an earth colored solid.

후처리

  1. stirringAfter stirring for one hour
  2. filtrationThe 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 (6×), sat. NaHCO3 (2×), brine (3×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customtriturated with ether

출처 및 근거

ORD 기록
ord-e202a04d313f4590937d5e1a0386b9b2
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677368B2

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