HCID 21831180, compound → HCID 21831175, compound

HRID 1601145Notes

Reaction equation

HRID 1601145 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH2:5][C:6]1[C:11]([N+:12]([O-])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[H][H]>[Pt].CN1CCOCC1>[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH2:5][C:6]1[C:11]([NH:12][OH:13])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 21831180HCID 21831180, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21831175HCID 21831175, compoundYield 161.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 79724-MethylmorpholineSolvent

Procedure

A mixture of 5.0 g (21 mmol) of 2-(2-methylphenoxymethyl)-3-nitropyridine (Example 3.d) and 100 ml of N-methylmorpholine was hydrogenated at room temperature (approximately 25° C.) and an H2 pressure of approximately 1.1 bar in the presence of 1 g of 5% platinum/charcoal (51% water; manufactured by Degussa). The hydrogen uptake ceased after approximately 90 minutes. The catalyst was removed by filtration through active charcoal. The resulting solution was freed from solvent under reduced pressure, and the residue obtained was treated with approximately 50 ml of petroleum ether. This gave 7.8 g (90%) of the title compound as a white solid. The solvent was removed under reduced pressure ("high vacuum"), and the residue obtained was washed using hexane. This gave 4.5 g (94%) of the title compound as a white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. custom(approximately 25° C.)
  3. customThe catalyst was removed by filtration through active charcoal
  4. customthe residue obtained

Sources & evidence

ORD record
ord-f1096a67342c42c59d4c1d0f1c7e5f70
Source dataset
uspto-grants-1999_11
Patent number
US05977146

Reaction notes

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