HCID 22157539, compound → HCID 86743504, compound

HRID 2248473Notes

Reaction equation

HRID 2248473 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH+:10]([O-:20])[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([O-])=O>C(O)C.[Pt]=O>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH+:10]([O-:20])[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1

Participants

4

Reactant 1

HCID 22157539HCID 22157539, compound

Product 1

HCID 86743504HCID 86743504, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(4-nitro-3-pyridinyl)-1H-indol-1-amine N1 -oxide (5 g) and 0.5 g of platinum oxide in 250 ml of ethanol was hydrogenated at 50 psi (pounds per square inch) for four hours. The mixture was filtered and the filtered liquid was concentrated to a dark residue which was purified by flash chromatography (silica, 10% methanol in dichloromethane) to give 2.5 g of solid, d 235°. This material was recrystallized from methanol/ether to give 2.1 g of crystals, d 235°.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtered liquid was concentrated to a dark residue which
  3. customwas purified by flash chromatography (silica, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7bfa32cb1fda4741b2061c27ad4be744
Source dataset
uspto-grants-1991_08
Patent number
US05039811

Reaction notes

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