N-(1-adamantyl)-3-(3-nitro-4-aminophenyl)propionamide → HCID 19038182, compound

HRID 263468Notes

Reaction equation

HRID 263468 reaction equation
[C:1]12([NH:11][C:12](=[O:25])[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([N+:22]([O-])=O)[CH:16]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>CO.[Pd]>[C:1]12([NH:11][C:12](=[O:25])[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([NH2:22])[CH:16]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 1

HCID 19038183N-(1-adamantyl)-3-(3-nitro-4-aminophenyl)propionamide

Product 1

HCID 19038182HCID 19038182, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

500 mg of N-(1-adamantyl)-3-(3-nitro-4-aminophenyl)propionamide (prepared as described in Example 21) was dissolved in 20 ml of methanol. 200 mg of 10% w/w palladium-on-carbon was added to the solution, which was then catalytically reduced whilst bubbling hydrogen through it, under atmospheric pressure for 120 minutes. The catalyst was then removed by filtration, and the methanol was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using 19:1 ethyl acetate:methanol as the eluent, to afford 0.21 g of the title compound as crystals, melting at 151°-152° C.

Workup

  1. customwhilst bubbling hydrogen through it
  2. customThe catalyst was then removed by filtration
  3. customthe methanol was removed by distillation under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99ef0b639bd24eb8988d8f5cda909685
Source dataset
uspto-grants-1997_07
Patent number
US05643925

Reaction notes

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