HCID 21490888, compound → HCID 21490910, compound

HRID 1973904Notes

Reaction equation

HRID 1973904 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([CH2:11][CH2:12][CH2:13][CH3:14])=[C:6](Cl)[N:5]=1)(=[O:3])[NH2:2].C(C1C=C(Cl)C(CCCC)=C(N)N=1)(=O)N.[H][H]>CO.[Pd]>[C:1]([C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([CH2:11][CH2:12][CH2:13][CH3:14])=[CH:6][N:5]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 21490888HCID 21490888, compoundHCID 21490889HCID 21490889, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21490910HCID 21490910, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

11.4 g (0.05 mol) of the isomer mixture of 2-carbamoyl-4-amino-5-n-butyl-6-chloro-pyridine and 2-carbamoyl-4-chloro-5-n-butyl-6-amino-pyridine, dissolved in 120 ml of pure methanol, are hydrogenated in the presence of 1.5 g of palladium on charcoal. After the calculated amount of hydrogen has been taken up, the catalyst is filtered off and the filtrate is evaporated to dryness. The residue is rendered alkaline with 2 N sodium carbonate solution and extracted with ether. The crystalline product which is soluble in neither sodium carbonate solution nor in ether is filtered off and rinsed with water. The white crystals are dried for 20 hours at 70° in a high vacuum. 2-Carbamoyl-4-amino-5-n-butyl-pyridine of the formula ##STR33## and of melting point 186°-190° is thus obtained.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated to dryness
  3. extractionextracted with ether
  4. filtrationis filtered off
  5. washrinsed with water
  6. customThe white crystals are dried for 20 hours at 70° in a high vacuum

Sources & evidence

ORD record
ord-edda81be66b0466e8efbc3d7a765f108
Source dataset
uspto-grants-1976_12
Patent number
US03998955

Reaction notes

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