Ethanol → HCID 178478666, compound

HRID 2269535Notes

Reaction equation

HRID 2269535 reaction equation
C(O)C.[N+:4]([C:7]1[N:8]=[C:9]([CH:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[NH:10][CH:11]=1)([O-])=O.C(OCC)C.C(Cl)[Cl:32]>[Pd]>[ClH:32].[ClH:32].[NH2:4][C:7]1[N:8]=[C:9]([CH:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[O:14])[NH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 178520208HCID 178520208, compound

Product 1

HCID 178478666HCID 178478666, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
60 °C

Procedure

Ethanol (200 mL) was added to a mixture of 2-(4-nitroimidazolyl)-2-phenyl-1-pyrrolidinylethan-1-one (3) (0.752 g, 2.8 mm) and 10% Pd on carbon (75 mg) in a Bradley hydrogenation apparatus. The stirred reaction mixture was subjected to a 60 psi H2 atmosphere and warmed to 60° C. After 2 hours, the reaction mixture was cooled to room temperature and the catalyst was removed by filtration. Anhydrous HCl gas was added to the filtered solution until saturation. The volatiles were then removed under vacuum to give a light yellow foam. Diethyl ether and methylene chloride (25:1) were added to the foam and the resulting mixture was stirred overnight to achieve crystallization. The resulting slurry was filtered and the cake was washed with diethyl ether. The cake was dried under vacuum to give 0.659 g (93%) of a yellow solid. LGD 208.

Workup

  1. customThe stirred reaction mixture
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customthe catalyst was removed by filtration
  4. additionAnhydrous HCl gas was added to the filtered solution until saturation
  5. customThe volatiles were then removed under vacuum
  6. customto give a light yellow foam
  7. customcrystallization
  8. filtrationThe resulting slurry was filtered
  9. washthe cake was washed with diethyl ether
  10. customThe cake was dried under vacuum

Sources & evidence

ORD record
ord-2ab97d1fe1a945b7be40a09d933138a1
Source dataset
uspto-grants-2001_12
Patent number
US06329342B1

Reaction notes

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