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

HRID 1587829Notes

Reaction equation

HRID 1587829 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>C(O)C.[Pt]=O>[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

4

Reactant 1

HCID 197564132-[2-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]ethoxy]-5-nitropyridine

Product 1

HCID 19756412HCID 19756412, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Compound B (36.8 g) was dissolved in ethanol (270 ml) and catalytically hydrogenated at atmospheric pressure over platinum oxide (300 mg). The catalyst was removed by filtration through diatomaceous earth. The solvent was removed by evaporation and the residue triturated with hexane to give 5-amino-2-[2-(trimethylsilyl)ethoxy]pyridine (C) (20.0 g), as dark crystals, m.p. 59°-61° C.; NMR: 0.0(s,9H), 0.95-1.05(m,2H), 3.1-3.3(br s, 2H), 4.2-4.3(m,2H), 6.5(d,1H), 6.95(dd,1H), 7.6(d,1H).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customThe solvent was removed by evaporation
  3. customthe residue triturated with hexane

Sources & evidence

ORD record
ord-c216ed21b0b44112991094e3d82f90c0
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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