Acetic Acid → HCID 22561914、化合物

HRID 983029ノート

反応式

HRID 983029 の反応式
[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]

参加物

8

反応物 4

HCID 176Acetic Acid2 回HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 225616844-(3,4-dimethoxy-phenyl)1H-indole

生成物 1

HCID 22561914HCID 22561914、化合物収率 65%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-92d31f892f444d61b8be89c4eb00fc2e
出典データセット
uspto-grants-2005_03
特許番号
US06861418B2

反応ノート

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