HCID 22117695, compound → HCID 22117692, compound

HRID 1275681Notes

Reaction equation

HRID 1275681 reaction equation
C([O:8][C:9]1[CH:27]=[CH:26][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][C:15]=2[N+:23]([O-])=O)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.O1CCCC1.[C].[Pd]>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:12]2[CH:26]=[CH:27][C:9]([OH:8])=[CH:10][CH:11]=2)=[C:15]([CH:16]=1)[NH2:23])[CH3:22]

Participants

5

Reactant 1

HCID 22117695HCID 22117695, compound

Product 1

HCID 22117692HCID 22117692, compoundYield 91.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(benzyloxy)phenoxy]-3-nitrophenetole (4.26 g, 11.7 mmol) in a mixture of ethanol (70 ml) and tetrahydrofuran (50 ml) was added 10% palladium-carbon (430 mg), followed by stirring under a hydrogen gas atmosphere at room temperature overnight. After removal of the insoluble matter by filtration, the solvent was evaporated under reduced pressure. The resulting crude crystals were recrystallized from a mixture of ethyl acetate and hexane (1:9) to give the title compound (2.63 g).

Workup

  1. customAfter removal of the insoluble matter
  2. filtrationby filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting crude crystals were recrystallized from a mixture of ethyl acetate and hexane (1:9)

Sources & evidence

ORD record
ord-c5cb0712155142578d8b49590c4dcc06
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

Loading…