HCID 53654476, compound → HCID 67656043, compound

HRID 1458344Notes

Reaction equation

HRID 1458344 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=2)[NH:12][C:11]=1[C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pt](=O)=O>[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=2)[NH:12][C:11]=1[C:22]1[CH:23]=[C:24]([CH3:29])[CH:25]=[C:26]([CH3:28])[CH:27]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 53654476HCID 53654476, compound

Product 1

HCID 67656043HCID 67656043, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (0.4 g) was dissolved in methanol (25 mL) and platinum (IV) oxide (40 mg) added. The mixture was placed on a Parr hydrogenation apparatus and hydrogenated at 45psi for 4 h; by this time the starting material had been consumed and converted into one product. The catalyst was removed by filtration and the filtrates evaporated under reduced pressure using a rotary evaporator and the final traces of solvent removed by using a high vacuum overnight. The amine (338 mg) was obtained as a powder.

Workup

  1. customby this time the starting material had been consumed
  2. customThe catalyst was removed by filtration
  3. customthe filtrates evaporated under reduced pressure
  4. customa rotary evaporator
  5. customthe final traces of solvent removed
  6. customa high vacuum overnight

Sources & evidence

ORD record
ord-aada455a64d444aab08bf51a7d4092a3
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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