Ethanol → HCID 86694305, compound

HRID 69099Notes

Reaction equation

HRID 69099 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[N:11]=[CH:10][CH:9]=2)=[C:4]([N+:18]([O-])=O)[CH:3]=1.O1CCCC1.C(O)C.[Cl-].[NH4+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[N:11]=[CH:10][CH:9]=2)=[C:4]([CH:3]=1)[NH2:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 866943065-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole

Product 1

HCID 86694305HCID 86694305, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 980 mg of 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole, 9.8 mL of tetrahydrofuran, 19.6 mL of ethanol, and 2.9 mL of water was added 102 mg of ammonium chloride, followed by heating at 70° C. 1.03 g of reduced iron was added thereto, followed by heating to reflux for 4 hours, and cooling to room temperature. The insoluble material was filtered through celite, the filtrate was concentrated, and a mixture of chloroform/water was added thereto. The aqueous layer was separated, and then the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 815 mg of 5-bromo-2-(1-cyclopentyl-1H-pyrazol-5-yl)aniline.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 4 hours
  3. temperaturecooling to room temperature
  4. filtrationThe insoluble material was filtered through celite
  5. concentrationthe filtrate was concentrated
  6. additiona mixture of chloroform/water
  7. additionwas added
  8. customThe aqueous layer was separated
  9. washthe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f3c6bf8d61d947d2812926e39b822455
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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