HCID 23339835, compound → HCID 23339816, compound

HRID 28253Notes

Reaction equation

HRID 28253 reaction equation
[N+:1]([C:4]1[C:5](=[O:19])[N:6]([CH2:16][CH2:17][CH3:18])[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O.[H][H]>[Ni].CN(C)C=O>[NH2:1][C:4]1[C:5](=[O:19])[N:6]([CH2:16][CH2:17][CH3:18])[CH:7]=[C:8]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 23339835HCID 23339835, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23339816HCID 23339816, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution containing 15.1 g. of 3-nitro-1-n-propyl-5-(4-pyridinyl)-2(1H)-pyridinone in 400 ml. of dry dimethylformamide was charged into an 800 ml. Parr bottle with 1.5 teaspoons of Raney nickel and the mixture was shaken under 650 p.s.i of hydrogen at room temperature for four hours, during which time the reaction temperature was no more than 50° C. The catalyst was filtered off; the filtrate was treated with decolorizing charcoal and filtered; and, the solvent was distilled off under reduced pressure to leave 12.7 g. of crystalline solid. The solid was recrystallized from methanol to yield 7.2 g. of crystalline 3-amino-1-n-propyl-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 171°-173° C. after drying at 70° C. and 0.001 mm. for six hours.

Workup

  1. additionA solution containing 15.1 g
  2. customwas no more than 50° C
  3. filtrationThe catalyst was filtered off
  4. additionthe filtrate was treated with decolorizing charcoal
  5. filtrationfiltered
  6. distillationand, the solvent was distilled off under reduced pressure
  7. customto leave 12.7 g
  8. customThe solid was recrystallized from methanol
  9. customto yield 7.2 g
  10. dry with materialof crystalline 3-amino-1-n-propyl-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 171°-173° C. after drying at 70° C.

Sources & evidence

ORD record
ord-6c3b7a07e4cb49bc94c67e43fd8dbdad
Source dataset
uspto-grants-1980_09
Patent number
US04225715

Reaction notes

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