Acetic Acid → HCID 13424431, compound

HRID 1249160Notes

Reaction equation

HRID 1249160 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-d8af008e8cfd48b5a4f5a2a4ae37bbd5
Source dataset
uspto-grants-1986_12
Patent number
US04629735

Reaction notes

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