Methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate → Methyl 2-(3,5-dichloro-4-hydroxyphenylamino)benzoate

HRID 883819Notes

Reaction equation

HRID 883819 reaction equation
C([O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:11][C:10]=1[Cl:27])C1C=CC=CC=1>[Pd].C1COCC1>[Cl:15][C:14]1[CH:13]=[C:12]([NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])[CH:11]=[C:10]([Cl:27])[C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 59509768Methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate

Product 1

HCID 59509759Methyl 2-(3,5-dichloro-4-hydroxyphenylamino)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on carbon (10% by mass of 10% by wt Pd, 50 mg) was cautiously added to a deoxygenated stirring solution of methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate (0.520 g, 1.3 mmol) in THF (15 mL). The mixture was subjected to three cycles of evacuation and purging with hydrogen gas, before being stirred under an atmosphere of hydrogen gas. After 3 h, the reaction was purged with nitrogen, filtered through Celite™ (eluent: THF) and concentrated in vacuo to afford methyl 2-(3,5-dichloro-4-hydroxyphenylamino)benzoate as a white solid that was used without further purification.

Workup

  1. custompurging with hydrogen gas
  2. customthe reaction was purged with nitrogen
  3. filtrationfiltered through Celite™ (eluent: THF)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bde8d590a624b9e8e29c4ca16a04b98
Source dataset
uspto-grants-2012_08
Patent number
US08236984B2

Reaction notes

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