4-methyl-N-(alpha-phenylethyl)phenoxazine → 4-Methyl-10H-phenoxazine

HRID 1381655Notes

Reaction equation

HRID 1381655 reaction equation
[CH3:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7](C(C3C=CC=CC=3)C)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[CH3:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 140312584-methyl-N-(alpha-phenylethyl)phenoxazineHCID 178418361HCID 178418361, compound

Product 1

HCID 140312634-Methyl-10H-phenoxazine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-methyl-N-(α-phenylethyl)phenoxazine in 30 ml of ethyl acetate and 130 ml of ethanol was hydrogenated at atmospheric pressure (585 mm Hg) in the presence of 1.5 g of 10% palladium-charcoal as catalyst, until the calculated amount of hydrogen was consumed (16 hours). The catalyst was then separated by filtration through celite and the solvent removed under reduced pressure. Chromatography of the solid residue (1 g) on 100 g of silica gel in a column, using hexane-ethyl acetate (80:20) as the eluting solvent produced 4-methylphenoxazine, a white solid, which was recrystallized from pentane, mp: 91° C.

Workup

  1. customwas consumed (16 hours)
  2. customThe catalyst was then separated by filtration through celite
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c3d7d7623a904b84938ba1f129352e0f
Source dataset
uspto-grants-1989_02
Patent number
US04803269

Reaction notes

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