Dimethylformamide → HCID 12940912, compound

HRID 2058525Notes

Reaction equation

HRID 2058525 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[N:3]=1.CN(C)C=O>[Pd].C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 12940911HCID 12940911, compound

Product 1

HCID 12940912HCID 12940912, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture containing 43.2 g. of 2-amino-3-nitro-6-(4-pyridinyl)pyridine, 360 ml. of dimethylformamide, 220 ml. of ethanol and 1 g. of 10% palladium-on-charcoal was shaken in a Parr apparatus under catalytic hydrogenation conditions for about one hour. The reaction mixture was filtered and the filtrate concentrated in vacuo to a volume of about 150 ml. and cooled. The separated solid was collected and dried to produce 20 g. of 2,3-diamino-6-(4-pyridinyl)pyridine which can be used directly in the next step without further purification. In another run, a sample was recrystallized from ethanol using decolorizing charcoal to produce the product, 2,3-diamino-6-(4-pyridinyl)pyridine, melting at 252°-254° C.

Workup

  1. additionA mixture containing 43.2 g
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo to a volume of about 150 ml
  4. temperatureand cooled
  5. customThe separated solid was collected
  6. customdried
  7. customto produce 20 g
  8. customof 2,3-diamino-6-(4-pyridinyl)pyridine which can be used directly in the next step without further purification
  9. customIn another run, a sample was recrystallized from ethanol using

Sources & evidence

ORD record
ord-b613f900298b45d586dc142a8d375ace
Source dataset
uspto-grants-1982_03
Patent number
US04317909

Reaction notes

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