Formaldehyde → HCID 68205823, compound

HRID 333537Notes

Reaction equation

HRID 333537 reaction equation
O.[C:2]1([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[CH:18]([O-])=O.[NH4+]>[Pd].CO>[CH3:18][NH:15][C:14]1[C:9]([NH:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 2723923Ammonium formateHCID 106790912-N-phenylpyridine-2,3-diamine

Product 1

HCID 68205823HCID 68205823, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%, 11.49 g) was added to a three-neck flask. A gentle nitrogen flow was applied to the flask. Water (40 mL) and methanol (800 mL) were added to the flask. Then, N2-phenylpyridine-2,3-diamine (20 g, 108 mmol), formaldehyde (8.76 g, 108 mmol), and ammonium formate (136 g, 2160 mmol) were added. The reaction was stirred at room temperature overnight. The solution was filtered through a Celite® plug. The filtrate was concentrated and water was added. The solution was extracted with dichloromethane. The combined organic layer was concentrated and purified by column chromatography (30% ethyl acetate in hexanes) to give N3-methyl-N2-phenylpyridine-2,3-diamine (12 g, 55.8% yield).

Workup

  1. filtrationThe solution was filtered through a Celite® plug
  2. concentrationThe filtrate was concentrated
  3. additionwater was added
  4. extractionThe solution was extracted with dichloromethane
  5. concentrationThe combined organic layer was concentrated
  6. custompurified by column chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3252c8ac195f4529ac381bd49c2fe928
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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