Ethanol → HCID 14835239, compound

HRID 1084904Notes

Reaction equation

HRID 1084904 reaction equation
Cl.[CH3:2][NH:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH2:5]1.Br[CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C(#N)C>[CH3:2][N:3]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH2:5]1)[CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneHCID 14835238HCID 14835238, compound

Product 1

HCID 14835239HCID 14835239, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methylamino-5-nitroindane hydrochloride (0.46 g), 2-bromoethoxy-4-nitrobenzene (0.49 g) [see C.A., (1960), 54, 11046a] and potassium carbonate (2 g) were heated under reflux in acetonitrile (50 ml)/ethanol (20 ml) for 20 hours. The solvent was then removed by evaporation in vacuo and the residue diluted with water and extracted with methylene chloride. The organic layer was dried (MgSO4) and evaporated to give an oil which was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated to give the title compound as an oil, yield 0.28 g.

Workup

  1. customThe solvent was then removed by evaporation in vacuo
  2. additionthe residue diluted with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by column chromatography on silica eluting with methylene chloride
  8. additioncontaining methanol (0% up to 1%)
  9. customevaporated

Sources & evidence

ORD record
ord-607219b7e93a42298283eb2b0c415916
Source dataset
uspto-grants-1991_04
Patent number
US05006561

Reaction notes

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