HCID 27514272, compound → HCID 20670049, compound

HRID 380696Notes

Reaction equation

HRID 380696 reaction equation
[CH3:1][C:2]1[C:21]([N+:22]([O-])=O)=[CH:20][C:19]([N+:25]([O-])=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]>C(OCC)(=O)C.[Pd]>[NH2:22][C:21]1[C:2]([CH3:1])=[C:3]([CH:18]=[C:19]([NH2:25])[CH:20]=1)[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

4

Reactant 1

HCID 27514272HCID 27514272, compound

Product 1

HCID 20670049HCID 20670049, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-3,5-dinitro-N-(tricyclo[3.3.1.13.7]dec-1-ylmethyl)-benzamide (Example 65) (2.66 g) in ethyl acetate (200 ml) was hydrogenated over palladium on carbon (10%, 0.5 g ) for 72 hours. The reaction mixture was then filtered through celite® and the residue washed with ethyl acetate. The filtrate and washings were combined and concentrated under reduced pressure to give a solid (0.8 g). This was purified by column chromatography over silica eluting with dichloromethane:ethanol (9:1). The product was further purified by treatment with charcoal in boiling ethanol followed by filtration and concentration to remove coloured impurities to give the title compound as a near colourless solid (0.58 g).

Workup

  1. filtrationThe reaction mixture was then filtered through celite®
  2. washthe residue washed with ethyl acetate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15221dfc62a9463c95a029d6bc446195
Source dataset
uspto-grants-2001_10
Patent number
US06303659B2

Reaction notes

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