4-(4-methoxy-2-nitrobenzylidene)tetrahydro-2H-pyran → 5-methoxy-2-(tetrahydro-2H-pyran-4-ylmethyl)aniline

HRID 1914681Notes

Reaction equation

HRID 1914681 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH:7]=[C:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:5]([N+:16]([O-])=O)[CH:4]=1.[H][H]>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:5]([CH:4]=1)[NH2:16]

Participants

5

Reactant 2

HCID 593531074-(4-methoxy-2-nitrobenzylidene)tetrahydro-2H-pyranHCID 178418361HCID 178418361, compound

Product 1

HCID 593530905-methoxy-2-(tetrahydro-2H-pyran-4-ylmethyl)anilineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-methoxy-2-nitrobenzylidene)tetrahydro-2H-pyran (1.8 g; 7.22 mmol; 1 eq) is dissolved in EtOH (100 mL) and palladium on charcoal (180 mg, 10%) is added at room temperature under argon. The solution is treated with hydrogen at atmospheric pressure. After 7 h at room temperature, the reaction is complete. The mixture is filtered through celite and the filtrate is concentrated under reduced pressure to afford 1.5 g (94%) of the title compound as an orange oil. 1H NMR (DMSO-d6) δ 6.72 (d, J=8.3 Hz, 1H), 6.18 (d, J=2.6 Hz, 1H), 6.04 (dd, J=8.3, 2.6 Hz, 1H), 4.82 (s, 2H), 3.82-3.77 (m, 2H), 3.62 (s, 3H), 3.19 (td, J=11.7, 1.8 Hz, 2H), 2.29 (d, J=6.8 Hz, 2H), 1.72-1.61 (m, 1H), 1.51-1.46 (m, 2H), 1.24-1.10 (m, 2H). HPLC (max plot) 88%; Rt 1.83 min LC/MS: (ES+): 222.4.

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a20b05ce11a041c8860f1f4c3e2073ad
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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