HCID 19756384, compound → HCID 19756366, compound

HRID 893622Notes

Reaction equation

HRID 893622 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[N:8][CH:9]=1)([O-])=O>C(O)C.[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 19756384HCID 19756384, compound

Product 1

HCID 19756366HCID 19756366, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

5-Nitro-2-[2-(trimethylsilyl)ethoxy]pyridine (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 (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-95a0f27467954dc0990d330ffd0fd212
Source dataset
uspto-grants-1992_06
Patent number
US05126344

Reaction notes

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