HCID 67236094, compound → HCID 67236645, compound

HRID 1505343Notes

Reaction equation

HRID 1505343 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][C:11]1[N:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 67236094HCID 67236094, compound2×

Product 1

HCID 67236645HCID 67236645, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-{[2-methyl-5-(methyloxy)phenyl]oxy}-5-nitropyridine (Intermediate 53, 1.5 g) in ethanol (100 mL) was added Pd/C (5%, 200 mg) and the mixture was stirred at room temperature under H2 atmosphere overnight. The mixture was filtered through a pad of celite and the filtrate was evaporated to afford a yellow oil, which was purified by column chromatography on silica gel (mobile phase: EtOAc/PE=1/5−1/2). This afforded the title compound (850 mg).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated
  3. customto afford a yellow oil, which
  4. customwas purified by column chromatography on silica gel (mobile phase: EtOAc/PE=1/5−1/2)

Sources & evidence

ORD record
ord-496c0d1a25344285b6e787c187034996
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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