HCID 53966654, compound → HCID 12640164, compound

HRID 1680458Notes

Reaction equation

HRID 1680458 reaction equation
[CH2:1]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[N:15][CH:16]=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>[OH-].[Na+].C(O)C.[Pd]>[C:4]1([CH2:3][CH2:2][CH2:1][NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[N:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 53966654HCID 53966654, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12640164HCID 12640164, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

3 g of 5-cinnamylamino pyridine-2-carboxylic acid are dissolved in 50 ml of 0.5 N aqueous sodium hydroxide containing 1 ml of ethanol and the solution is hydrogenated over 0.5 g of 10% palladium on charcoal at atmospheric pressure and room temperature. After the hydrogen uptake has ceased, the mixture is filtered and the filtrate acidified with hydrochloric acid. The solution is extracted with ethyl acetate, the extract washed with water, dried, evaporated and the residue crystallized from methanol, to yield the 5-(3-phenylpropylamino)-pyridine-2-carboxylic acid melting at 167°-169°.

Workup

  1. filtrationthe mixture is filtered
  2. extractionThe solution is extracted with ethyl acetate
  3. washthe extract washed with water
  4. customdried
  5. customevaporated
  6. customthe residue crystallized from methanol

Sources & evidence

ORD record
ord-2189cc30e195456eacb793c351ae6097
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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