Hydrochloric Acid → HCID 13649441, compound

HRID 280213Notes

Reaction equation

HRID 280213 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[N:13]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].Cl.[H][H]>CO.[Pd]>[NH2:19][CH2:18][C:14]1[N:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14097204HCID 14097204, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13649441HCID 13649441, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(p-Ethoxycarbonylphenyl)-6-cyanopyridine (16.23 g) is hydrogenated at atmospheric pressure in 254 ml of methanol with 12.9 ml of concentrated hydrochloride acid and 2.63 g of 10% palladium on charcoal until 2 molar equivalents of hydrogen have been consumed. Sodium methoxide (6.9 g) is added and the catalyst is filtered off. The solvent is evaporated. The residue is redissolved in 20 ml of methylene chloride and the salts are removed by filtration. Evaporation of the solvent yields a solid which is recrystallized from chloroform to yield 6-aminomethyl-2-(p-ethoxycarbonylphenyl)pyridine, m.p. 141°-143°.

Workup

  1. customhave been consumed
  2. additionSodium methoxide (6.9 g) is added
  3. filtrationthe catalyst is filtered off
  4. customThe solvent is evaporated
  5. dissolutionThe residue is redissolved in 20 ml of methylene chloride
  6. customthe salts are removed by filtration
  7. customEvaporation of the solvent
  8. customyields a solid which
  9. customis recrystallized from chloroform

Sources & evidence

ORD record
ord-b2bf3251255e4117800d7dcf560b60ca
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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