Formic Acid → 2,4-Diaminonicotinaldehyde

HRID 3416

Reaction equation

HRID 3416 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5](C#N)=[CH:4][N:3]=1.[CH:11]([OH:13])=O.[H][H]>[Ni].O>[NH2:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]([NH2:8])[C:7]=1[CH:11]=[O:13]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2958964,6-DiaminonicotinonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 218500292,4-Diaminonicotinaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A suspension of 13.4 g of 2,4-diamino-5-cyanopyridine from Example 14, 2 g of Raney nickel catalyst, 40 mL of 97-100% formic acid, and 80 mL of water were shaken in a Parr apparatus under an atmosphere of nitrogen until the requisite amount of hydrogen was consumed. The solvents were removed under reduced pressure and the residue treated with 17 mL of concentrate HCl. The resulting pink solid was slurried in a small amount of water, filtered, washed with isopropyl alcohol, followed by diethylether, and dried. Crystallization from ethanol afforded 6.5 g of the title compound 2,4-diaminonicotinaldehyde.

Workup

  1. customwas consumed
  2. customThe solvents were removed under reduced pressure
  3. additionthe residue treated with 17 mL of concentrate HCl
  4. filtrationfiltered
  5. washwashed with isopropyl alcohol
  6. customdried
  7. customCrystallization from ethanol

Sources & evidence

ORD record
ord-66fceab868444128830a463ef7b06941
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

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