N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)carbanilic acid benzyl ester → 4-(Ethylamino)-3,5-dimethoxy-benzoic acid methyl ester

HRID 414543Notes

Reaction equation

HRID 414543 reaction equation
C(OC(=O)[N:10]([CH2:25][CH3:26])[C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:12]=1[O:23][CH3:24])C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:22][O:21][C:19](=[O:20])[C:14]1[CH:15]=[C:16]([O:17][CH3:18])[C:11]([NH:10][CH2:25][CH3:26])=[C:12]([O:23][CH3:24])[CH:13]=1

Participants

5

Reactant 2

HCID 53836153N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)carbanilic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 545569364-(Ethylamino)-3,5-dimethoxy-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 77.5 g. of N-ethyl-2,6-dimethoxy-4-(methoxy-carbonyl)-carbanilic acid benzyl ester in 1 liter of methanol was hydrogenated in the presence of 2 g. of palladium on carbon (5%) until hydrogen uptake ceased. The suspension was heated to boiling and filtered. The filtrate was evaporated under vacuum. After recrystallization of the residue from cyclohexane, there was obtained 4-(ethylamino)-3,5-dimethoxy-benzoic acid methyl ester having a melting point of 50°-51° C.

Workup

  1. additionA suspension of 77.5 g
  2. temperatureThe suspension was heated
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum
  5. customAfter recrystallization of the residue from cyclohexane

Sources & evidence

ORD record
ord-addd8ee389714c36bed882ebea2f5da6
Source dataset
uspto-grants-1988_12
Patent number
US04792557

Reaction notes

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