Hydrochloric Acid → HCID 53912967, compound

HRID 1579315Notes

Reaction equation

HRID 1579315 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]#[N:13])=[C:6]([O:14][CH3:15])[CH:5]=1.Cl.[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([CH2:12][NH2:13])=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 54053300HCID 54053300, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53912967HCID 53912967, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

30 G. of 4-cyano-3,5-dimethoxy-benzoic acid methyl ester and 1500 ml. of methanol and 150 ml. of 1N hydrochloric acid is hydrogenated in the presence of 10 g. of palladium-on carbon 10% at room temperature and under atmospheric pressure. In about 5 hours, 2 moles of hydrogen are taken up. The solution is freed of the catalyst by filtration, evaporated to dryness and the residue is taken up in a little water. The solution is thereafter filtered, saturated with solid potassium carbonate and shaken with benzene. From the shaken benzene mixture, is obtained 4-(aminomethyl)-3,5-dimethoxy-benzoic acid methyl ester, which after recrystallization from high boiling petroleum ether has a m.p. of 81°-83°.

Workup

  1. customat room temperature
  2. filtrationThe solution is freed of the catalyst by filtration
  3. customevaporated to dryness
  4. filtrationThe solution is thereafter filtered, saturated with solid potassium carbonate

Sources & evidence

ORD record
ord-4934b3445366451599fd84e938b31243
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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