HCID 20079498, compound → HCID 15053103, compound

HRID 1588258Notes

Reaction equation

HRID 1588258 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)([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][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2

Participants

4

Reactant 1

HCID 20079498HCID 20079498, compound

Product 1

HCID 15053103HCID 15053103, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(4-nitro-3-pyridinyl)-1H-indol-5-amine, N5 -oxide (7.8 g) in 500 ml ethanol containing platinum oxide (1.25 g) was hydrogenated at 50 psi for six hours and thereafter filtered and concentrated. The product was purified by flash chromatography (silica, 20% methanol in dichloromethane) to give 6 g solid, m.p. 83°-90°. Three grams were distilled twice via Kugelrohr (240°-250° @ 0.01 mm Hg) to give 2.4 g solid, 138°-140°.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe product was purified by flash chromatography (silica, 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5635d3c4822a4a85b8475b636b821e48
Source dataset
uspto-grants-1993_06
Patent number
US05221682

Reaction notes

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