HCID 13371473, compound → HCID 13371474, compound

HRID 1719426Notes

Reaction equation

HRID 1719426 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[C:24](=[O:26])[CH3:25])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[C:24](=[O:26])[CH3:25])=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 13371473HCID 13371473, compound

Product 1

HCID 13371474HCID 13371474, compoundYield 80.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

1-[2-(4-Benzyloxyphenylamino)-5-methoxyphenyl]ethanone (9 g, 0.0258 mole) in 810 ml of ethanol and 90 ml of acetic acid was hydrogenated in a Parr apparatus in the presence of 900 mg of 10% palladium-on-carbon catalyst. After the required amount of hydrogen had been consumed, the reaction mixture was filtered and the solvents removed in vacuo. The residue was partitioned between ether and 10% aqueous sodium bicarbonate. The ether extracts were dried (MgSO4), the solvent removed, and the residue chromatographed on silica gel using chloroform as the eluant. There was obtained 5.33 g of 1-[2-(4-hydroxyphenylamino)-5-methoxyphenyl]ethanone, orange solid, m.p. 118°-119° C.

Workup

  1. customAfter the required amount of hydrogen had been consumed
  2. filtrationthe reaction mixture was filtered
  3. customthe solvents removed in vacuo
  4. customThe residue was partitioned between ether and 10% aqueous sodium bicarbonate
  5. dry with materialThe ether extracts were dried (MgSO4)
  6. customthe solvent removed
  7. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-9ac394cd47314ff493200348e08ade1c
Source dataset
uspto-grants-1985_09
Patent number
US04539429

Reaction notes

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