Hydrochloric Acid → HCID 118023217, compound

HRID 1482409Notes

Reaction equation

HRID 1482409 reaction equation
Cl.Cl.[NH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[NH2:4].[O-]CC.[Na+].[C:15](OC)(=[O:18])[CH:16]=[CH2:17].Cl>>[N:7]1[CH:8]=[CH:9][CH:10]=[C:5]([N:3]2[CH2:17][CH2:16][C:15](=[O:18])[NH:4]2)[CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 2723922Sodium ethoxideHCID 171324893-Hydrazinylpyridine dihydrochloride

Product 1

HCID 118023217HCID 118023217, compound

Procedure

In a four-neck round bottomed flask (250 mL) which contained 3-hydrazinopyridine dihydrochloride (18.2 g, 0.100 mol) was added sodium ethoxide (21 wt % in ethanol, 107 g, 0.330 mol). The temperature of the slurry rose to 33° C. over 5 minutes. The mixture was stirred at room temperature for 1.25 hours. To the light red tinted slurry was added methyl acrylate (18.0 mL, 0.200 mol) over 10 minutes, with the temperature rising from 25° C. to 35° C. The color of the slurry changed from light red to brown/green. The mixture was heated at 55° C. for 3 hours. After stirring at room temperature overnight, the mixture was neutralized to pH˜7 with hydrochloric acid (4 M in 1,4-dioxane, 32.6 g, 0.130 mol). The dark gray slurry was concentrated to a dark, paste like solid.

Workup

  1. customIn a four-neck round bottomed flask (250 mL) which contained
  2. customrising from 25° C. to 35° C
  3. temperatureThe mixture was heated at 55° C. for 3 hours
  4. stirringAfter stirring at room temperature overnight
  5. concentrationThe dark gray slurry was concentrated to a dark, paste like solid

Sources & evidence

ORD record
ord-acb1495a808047a1b5a1c829739fff49
Source dataset
uspto-grants-2016_08
Patent number
US09414594B2

Reaction notes

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