Calcium Chloride → (+/-)-(5-Amino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl)-(1,3,4,9-tetrahydro-beta-carboline-2-yl)-methanone

HRID 1987772노트

반응식

HRID 1987772 반응식
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]([C:16]1([CH3:31])[CH2:20][CH:19]2[CH:21]([CH3:30])[C:22]([N+:27]([O-])=O)=[C:23]([CH3:26])[C:24]([CH3:25])=[C:18]2[O:17]1)=[O:15].[Cl-].[Ca+2].[Cl-]>[Zn].C(O)C>[NH2:27][C:22]1[C:23]([CH3:26])=[C:24]([CH3:25])[C:18]2[O:17][C:16]([C:14]([N:2]3[CH2:3][CH2:4][C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[NH:12][C:13]=4[CH2:1]3)=[O:15])([CH3:31])[CH2:20][C:19]=2[C:21]=1[CH3:30]

참가 물질

5

반응물 2

HCID 5284359Calcium ChlorideHCID 68846049(+/-)-(1,3,4,9-Tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone

생성물 1

HCID 23118280(+/-)-(5-Amino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl)-(1,3,4,9-tetrahydro-beta-carboline-2-yl)-methanone수율 38.1%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 702Ethanol용매

실험 절차

0.54 g of (±)-(1,3,4,9-tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone, 1.86 g of zinc, 0.19 g of calcium chloride dehydrate and 30 ml of ethanol were added, followed by heating at reflux overnight. The insoluble matter was filtered through celite and the solvent was distilled off. The reaction solution was mixed with water, extracted with chloroform, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:ethyl acetate=50:1) to obtain 0.19 g of the objective product (melting point: 129-133° C.)

후처리

  1. temperatureby heating
  2. temperatureat reflux overnight
  3. filtrationThe insoluble matter was filtered through celite
  4. distillationthe solvent was distilled off
  5. additionThe reaction solution was mixed with water
  6. extractionextracted with chloroform
  7. washwashed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationafter the solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=50:1)

출처 및 근거

ORD 기록
ord-025cdb3cfeb84dca8c23b45e09e29315
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553837B2

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