4-(3-(2-Nitropyridin-3-yloxy)phenyl)morpholine → 3-(3-Morpholinophenoxy)pyridin-2-amine

HRID 911892Notes

Reaction equation

HRID 911892 reaction equation
[N+:1]([C:4]1[C:9]([O:10][C:11]2[CH:12]=[C:13]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[O:20]1[CH2:21][CH2:22][N:17]([C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[O:10][C:9]2[C:4]([NH2:1])=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 669951694-(3-(2-Nitropyridin-3-yloxy)phenyl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 669950653-(3-Morpholinophenoxy)pyridin-2-amineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 125 mL round-bottom flask, 4-(3-(2-nitropyridin-3-yloxy)phenyl)morpholine (0.92 g, 3.05 mmol) was dissolved in 30 mL of ethanol and 200 mg of 10% Pd/C (Degussa type, 50% wet) added. The resulting mixture was agitated overnight under the atmospheric pressure of hydrogen. The mixture was filtered and the solvent was evaporated to give the title compound (0.80 g, 97%) as thick oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8729e005eb5e424684d1da2f5ebcbe10
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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