Ethanol → HCID 178419957, compound

HRID 1726392Notes

Reaction equation

HRID 1726392 reaction equation
C(O)C.C[N:5](C)/[CH:6]=[CH:7]/[C:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=O.O.[NH2:18]N>O>[NH:5]1[CH:6]=[CH:7][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:18]1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)2×HCID 5396716(2E)-3-(Dimethylamino)-1-(4-Pyridinyl)-2-Propen-1-One

Product 1

HCID 178419957HCID 178419957, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 mL absolute ethanol was added (E)-3-(dimethylamino)-1-(pyridin-4-yl)prop-2-en-1-one (20 g; Example 1, Step 1). When all solids dissolved, 6.33 mL hydrazine monohydrate was added dropwise with stirring. After 30 minutes an additional 1.1 mL hydrazine hydrate was added. After 2 hours the reaction was treated with water and the yellow solution was concentrated under vacuum until a slurry formed. The resulting solid product was collected by vacuum filtration, washed with water, and dried under high vacuum overnight to yield 15.27 g (93% yield) of product as off-white crystals. 1H NMR (CDCl3) was consistent with a tautomeric mixture of the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 146.4 by positive ESI.

Workup

  1. dissolutionWhen all solids dissolved
  2. concentrationthe yellow solution was concentrated under vacuum until a slurry
  3. customformed
  4. filtrationThe resulting solid product was collected by vacuum filtration
  5. washwashed with water
  6. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-0cc96a0806b44d69b77137f7d52df718
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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