2-[2-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]ethoxy]-5-nitropyridine → HCID 19756412, compound

HRID 1587825Notes

Reaction equation

HRID 1587825 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][N:23]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:23][CH:24]=1

Participants

5

Reactant 2

HCID 197564132-[2-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]ethoxy]-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 19756412HCID 19756412, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound B (106 g) was dissolved in methanol (1.35 l) and hydrogenated at atmospheric pressure over 10% palladium on charcoal catalyst (10.6 g). When hydrogen uptake was complete, the catalyst was removed by filtration through diatomaceous earth. Volatile material was then removed from the filtrate by evaporation to give 5-amino-2-[2-(t-butyldiphenylsilyl)oxyethoxy]pyridine (C) (99.4 g), as an oil which was used without further purification; NMR (d6 -DMSO): 0.95(s,9H), 3.9(t,2H), 4.25(t,2H), 4.7(brs,2H), 6.5(d,1H), 7.0(dd,1H), 7.35-7.75 (complex m,7H), 7.6-7.75(m,4H).

Workup

  1. customthe catalyst was removed by filtration through diatomaceous earth
  2. customVolatile material was then removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-a8c3fda242c744a6834b25ab2199f53f
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

Loading…