Hydrazine hydrate (1:1) → HCID 178524552, compound

HRID 2281902Notes

Reaction equation

HRID 2281902 reaction equation
C[N:2](C)/[CH:3]=[CH:4]\[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=1)[C:10]([O:12]C)=[O:11])=O.O.[NH2:19]N>C(O)C>[NH:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=2)[C:10]([OH:12])=[O:11])=[N:19]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67151275HCID 67151275, compound

Product 1

HCID 178524552HCID 178524552, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a 2 L three-necked flask was added (Z)-methyl 2-(3-(dimethylamino)acryloyl)isonicotinate (0.894 mol), hydrazine hydrate (48.8 g), anhydrous ethanol (1 L). The suspension was stirred at 20° C. overnight. The solvent was removed in vacuo. The residue was taken up in concentrated hydrochloric acid (600 mL) and heated to reflux for 2 hours. The mixture was cooled to ambient temperature. The resultant precipitate was filtered, washed with water, ethanol and acetone and dried to give 78.6 g of the title compound as a brown solid. 1HNMR (DMSO-d6/D2O) δ ppm 8.80 (d, 1H), 8.50 (s, 1H), 7.91 (d, 1H), 7.87 (dd, 1H), 7.15 (d, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. temperatureheated
  3. temperatureto reflux for 2 hours
  4. temperatureThe mixture was cooled to ambient temperature
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with water, ethanol and acetone
  7. customdried

Sources & evidence

ORD record
ord-b2da21a7afed47748f520dd070871863
Source dataset
uspto-grants-2015_09
Patent number
US09139587B2

Reaction notes

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