2-[(4-Nitro-2-vinylphenoxy)methyl]pyridine → 3-Ethyl-4-(pyridin-2-ylmethoxy)aniline

HRID 550420Notes

Reaction equation

HRID 550420 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[C:6]([CH:18]=[CH2:19])[CH:5]=1)([O-])=O.[H][H]>C(O)C.O=[Pt]=O>[CH2:18]([C:6]1[CH:5]=[C:4]([CH:17]=[CH:16][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[NH2:1])[CH3:19]

Participants

5

Reactant 2

HCID 670206782-[(4-Nitro-2-vinylphenoxy)methyl]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 670207363-Ethyl-4-(pyridin-2-ylmethoxy)anilineYield 83%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-[(4-nitro-2-vinylphenoxy)methyl]pyridine (1.06 g, 4.16 mmol) and PtO2 (123 mg) in ethanol (100 ml) was stirred under an atmosphere of hydrogen until completion of the reaction (the reaction being complete when 4 mole equivalents of hydrogen have been reacted). After filtration on celite, the solvent was evaporated and the residue purified on silica gel (2% methanol/CH2Cl2) to give 3-ethyl-4-(pyridin-2-ylmethoxy)aniline (787 mg, 83%); NMR Spectrum: 1.12 (t, 3H), 2.53 (q, 2H), 4.56 (br s, 2H), 5.01 (s, 2H), 6.33 (dd, 1H), 6.43 (d, 1H), 6.69 (d, 1H), 7.32 (dd, 1H), 7.5 (d, 1H), 7.84 (t, 1H), 8.55 (d, 1H); Mass Spectrum: 229 (MH+).

Workup

  1. customhave been reacted)
  2. filtrationAfter filtration on celite
  3. customthe solvent was evaporated
  4. customthe residue purified on silica gel (2% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-3644fe749d20481eabc152fa292c93a9
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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