Acetic Acid → HCID 13424431, compound

HRID 462611Notes

Reaction equation

HRID 462611 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)(=O)C>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 13424428HCID 13424428, compound

Product 1

HCID 13424431HCID 13424431, compoundYield 122.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6 g of ethyl 2-(4-benzyloxyphenylamino)-5-methoxybenzoate, 30 ml of acetic acid, 270 ml of ethanol and 500 mg of 10% palladium-on-carbon catalyst was hydrogenated on a Parr apparatus for eight hours. The mixture was filtered, the filtrate stripped of solvent and the residue partitioned between ether and saturated sodium bicarbonate solution. The ether solution was dried over anhydrous magnesium sulfate and the solvent removed to give 5.6 g of ethyl 2-(4-hydroxyphenylamino)-5-methoxybenzoate as a yellow solid, m.p. 134°-136° C. when recrystallized from toluene.

Workup

  1. filtrationThe mixture was filtered
  2. customthe residue partitioned between ether and saturated sodium bicarbonate solution
  3. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  4. customthe solvent removed

Sources & evidence

ORD record
ord-5347d8f3094c4ed99c8bbff5fc964800
Source dataset
uspto-grants-1985_05
Patent number
US04515980

Reaction notes

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