Sodium Bicarbonate → HCID 25000402, compound

HRID 2381277Notes

Reaction equation

HRID 2381277 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:14]=[CH:15][N+:16]([O-:18])=[O:17])=[C:5]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O>[CH3:1][O:2][C:3]1[C:4]([CH:14]([CH2:15][N+:16]([O-:18])=[O:17])[CH2:15][N+:16]([O-:18])=[O:17])=[C:5]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[NH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68554815HCID 68554815, compound

Product 1

HCID 25000402HCID 25000402, compoundYield 125.4%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A solution of 5,7-dimethoxy-4-nitroethenylindole (0.82 g, 3.3 mmol) and NaHCO3 (0.33 g) in nitromethane (15 cm3) was refluxed under nitrogen for 30 hours. The mixture was then concentrated under reduced pressure and then partitioned between water (10 cm3) and ethyl acetate (10 cm3). The organic layer was washed with saturated aqueous NaHCO3 (10 cm3), then brine (10 cm3), dried over MgSO4 and evaporated under reduced pressure to give a crude solid, which was purified by chromatography on silica, eluting with petrol:ethyl acetate (80:20) to give 5,7-dimethoxy-4-{2′-nitro-1′-(nitromethyl)ethyl}indole as a pale yellow solid (0.64 g, 63%)

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. custompartitioned between water (10 cm3) and ethyl acetate (10 cm3)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (10 cm3)
  4. dry with materialbrine (10 cm3), dried over MgSO4
  5. customevaporated under reduced pressure
  6. customto give a crude solid, which
  7. customwas purified by chromatography on silica
  8. washeluting with petrol:ethyl acetate (80:20)

Sources & evidence

ORD record
ord-cf07b3d5aca2451b9209aa2c4230533c
Source dataset
uspto-grants-2012_09
Patent number
US08258173B2

Reaction notes

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