HCID 20079498, compound → HCID 15053103, compound

HRID 1654056Notes

Reaction equation

HRID 1654056 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-57bd21f75c714268b4b22e69ff9842de
Source dataset
uspto-grants-1995_04
Patent number
US05405856

Reaction notes

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