Formaldehyde → HCID 68205825, compound

HRID 333540Notes

Reaction equation

HRID 333540 reaction equation
CO.[C:3]1([CH3:17])[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:4]=1.C=O.[CH:20]([O-])=O.[NH4+]>O>[CH3:20][NH:16][C:15]1[C:10]([NH:9][C:5]2[CH:4]=[C:3]([CH3:17])[CH:8]=[CH:7][CH:6]=2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 2723923Ammonium formateHCID 22724430HCID 22724430, compound

Product 1

HCID 68205825HCID 68205825, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

600 mL of methanol and 24 mL water were added to a 3-neck 2 L round bottom flask. Nitrogen was bubbled directly into the solution. Palladium on carbon was added (10%, 10.35 g, 9.73 mmol) while bubbling continued. Next, N2-(m-tolyl)pyridine-2,3-diamine (19.38 g, 97 mmol) and formaldehyde (37%, 14.48 mL, 195 mmol) were added. The reaction mixture was stirred under nitrogen for 3 h. Next, nitrogen was bubbled into the solution and ammonium formate (123 g, 1945 mmol) was added slowly. The reaction mixture was stirred under nitrogen overnight at room temperature. The reaction mixture was filtered through Celite® and the Celite® was washed with dichloromethane. The filtrate was washed with water twice, and the organic layer was dried over magnesium sulfate, filtered, and evaporated. The residue was purified using column chromatography eluting with 30% ethyl acetate/hexanes to isolate the desired product. The product was combined with material from other reactions and purified by column chromatography eluting with 30% ethyl acetate/hexanes. A dark reddish-brown solid was obtained. The solid was recrystallized from boiling hexanes with a small amount of ethyl acetate to dissolve the solid. The product was filtered off as needles with some reddish color which were washed with hexanes, obtained 15.1 g.

Workup

  1. customNitrogen was bubbled directly into the solution
  2. additionPalladium on carbon was added (10%, 10.35 g, 9.73 mmol)
  3. customwhile bubbling
  4. additionwas added slowly
  5. stirringThe reaction mixture was stirred under nitrogen overnight at room temperature
  6. filtrationThe reaction mixture was filtered through Celite®
  7. washthe Celite® was washed with dichloromethane
  8. washThe filtrate was washed with water twice
  9. dry with materialthe organic layer was dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified
  13. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-64850bda6f184dc497ec6629a3345244
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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