Sodium Iodide → Nitrobenzene

HRID 9097

Reaction equation

HRID 9097 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 3-nitrophenol (837 mg, 6.02 mmole), 1-chloro-3-[imidazo-1-yl]-propane (871 mg, 1 eq), K2CO3 (3.3 gm, 4 eq) and NaI (1.0 gm, 1.1 eq) in DMF was heated at 120° C. for 6 hr. After cooling to RT, the reaction was filtered and the filter cake was washed with DMF. The solvent was removed from the filtrate and the residue was chromatographed (radial chromatography; 4 mm silica gel plate that was eluted with a step gradient of DCM containing 0, 1, 2.5, 5, 7.5% MeOH) to afford 400 mg of 3-[3-imidazo-1-ylpropyloxy]]-nitrobenzene. This was treated with 10% palladium on charcoal (400 mg) in EtOH under a hydrogen atmosphere for 4 hr. Removal of the catalyst and the solvent left 3-[3-imidazo-1-ylpropyloxy]]-aniline was then coupled with 319A as described for 570 to afford 576 (HPLC retention time (YMC ODS S5 4.6×30 mm): 1.33 min). Beginning with 4-nitrophenol and 1-chloro-3-[imidazo-1-yl]-propane 577 (HPLC retention time (YMC ODS S5 4.6×30 mm): 1.42 min) was prepared in a similar manner as 576.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction was filtered
  3. washthe filter cake was washed with DMF
  4. customThe solvent was removed from the filtrate
  5. customthe residue was chromatographed (radial chromatography
  6. wash4 mm silica gel plate that was eluted with a step gradient of DCM containing 0, 1, 2.5, 5, 7.5% MeOH)

Sources & evidence

ORD record
ord-4cce3d012348490bb45fe8a36bc03cd3
Source dataset
uspto-grants-2006_08
Patent number
US07091223B2

Linked notes

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