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 1987772Notes

Reaction equation

HRID 1987772 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

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.)

Workup

  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)

Sources & evidence

ORD record
ord-025cdb3cfeb84dca8c23b45e09e29315
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

Loading…