4-(3-methoxy-4-nitrophenoxy)tetrahydro-2H-pyran → 2-Methoxy-4-((tetrahydro-2H-pyran-4-yl)oxy)aniline

HRID 417313Notes

Reaction equation

HRID 417313 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)[O:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:13]=[CH:14][C:15]=1[NH2:16]

Participants

4

Reactant 1

HCID 592846694-(3-methoxy-4-nitrophenoxy)tetrahydro-2H-pyran

Product 1

HCID 582863412-Methoxy-4-((tetrahydro-2H-pyran-4-yl)oxy)anilineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Step C A suspension of 4-(3-methoxy-4-nitrophenoxy)tetrahydro-2H-pyran (0.4 g, 1.6 mmol) and Pd/C (Aldrich, 10%, 0.1 g) in ethyl acetate (10 mL) was vigorously shaken in a Parr under atmosphere of H2 (50 psi) for 0.5 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to give 2-methoxy-4-(tetrahydro-pyran-4-yloxy)-phenylamine as a light yellow oil (0.3 g, 85%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eb13eafd9c244902a4a6109147f47fb3
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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