Ethanol → HCID 89996202, compound

HRID 1480845Notes

Reaction equation

HRID 1480845 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([O:14][CH3:15])[CH:8]=2)[CH2:3][CH2:2]1.[H][H].C[CH2:19][OH:20]>[Pd]>[CH3:15][O:14][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH:13]=[CH:12][C:10]=1[NH:11][CH:19]=[O:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 89996077HCID 89996077, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89996202HCID 89996202, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 4-(3,6-dihydro-2H-pyran-4-yl)-2-methoxyaniline (Preparation 156, 206 mg, 1.004 mmol) in EtOH (10 mL) was treated with Pd/C (10% w/w, 50 mg, 0.047 mmol) and stirred in an atmosphere of hydrogen for 36 hours. The suspension was filtered over celite and concentrated in vacuo. The residue was dissolved in formic acid (6 mL) and heated to reflux for 2 hours. The solution was concentrated in vacuo and azeotroped with toluene twice. The residue was purified by silica gel column chromatography eluting with 0 to 30% EtOAc in cyclohexanes to give the title compound (165 mg, 70%).

Workup

  1. filtrationThe suspension was filtered over celite and
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in formic acid (6 mL)
  4. temperatureheated
  5. temperatureto reflux for 2 hours
  6. concentrationThe solution was concentrated in vacuo
  7. customazeotroped with toluene twice
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with 0 to 30% EtOAc in cyclohexanes

Sources & evidence

ORD record
ord-014428c5b9d5479198a17056f3dce688
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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