2,6-dimethoxy-4-(methoxy-carbonyl)-N-methyl-carbanilic acid benzyl ester → Methyl 3,5-dimethoxy-4-(methylamino)benzoate

HRID 462547Notes

Reaction equation

HRID 462547 reaction equation
C(O[C:9](=O)[N:10](C)[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][CH3:9])=[C:12]([O:23][CH3:24])[CH:13]=1

Participants

5

Reactant 2

HCID 542703972,6-dimethoxy-4-(methoxy-carbonyl)-N-methyl-carbanilic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 53774973Methyl 3,5-dimethoxy-4-(methylamino)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 33.5 g. of 2,6-dimethoxy-4-(methoxy-carbonyl)-N-methylcarbanilic acid benzyl ester in 1 liter of methanol was hydrogenated in the presence of 1.5 g. of palladium on carbon (5%) until the hydrogen uptake stopped. The suspension was heated to boiling and filtered. The filtrate was evaporated under vacuum and the residue recrystallized from cyclohexane, whereby there was obtained 3,5-dimethoxy-4-(methylamino)-benzoic acid methyl ester having a melting point of 49°-51° C.

Workup

  1. additionA suspension of 33.5 g
  2. temperatureThe suspension was heated
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum
  5. customthe residue recrystallized from cyclohexane

Sources & evidence

ORD record
ord-46b26abdb7df4d9c9a1da4735f72e746
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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