Ethanol → HCID 178489929, compound

HRID 2095165Notes

Reaction equation

HRID 2095165 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[C:11](=[N:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]#[N:13])=[CH:5][CH:4]=1.[OH2:23].[NH2:24][NH2:25].[CH2:26](O)C>>[CH3:26][O:23][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[N:14][NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([NH2:13])=[N:24][N:25]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 24654Hydrazine hydrate (1:1)HCID 86601951HCID 86601951, compound

Product 1

HCID 178489929HCID 178489929, compoundYield 92%

Procedure

To a warm suspension of 4-(4-methoxyphenyl)-3-oxo-2-(phenylhydrazono)butyronitrile (1 g, 3.4 mmol) in ethanol was slowly added a solution of hydrazine hydrate (204 mg, 4.08 mmol) in 10 mL of ethanol. The solution was heated to reflux and a brownish clear solution was obtained. After 2 hours of reflux, the solvent was removed in vacuo. The obtained oil was dissolved with minimum amount of isopropanol, and a yellow powder was precipitated by the addition of water. The title compound was isolated by filtration in a yield of 560 mg. The filtrate was further purified by column chromatography (CH2Cl2:MeOH=15:1) and an additional 370 mg of the title compound was obtained. The total yield was 92%. MS (m/z, ES+): 308 (M+1, 100%); 1H NMR (ppm, CDCl3) δ 7.77 (m, 2H), 7.43 (m, 2H), 7.38 (m, 1H), 7.21 (d, 2H), 6.86 (d, 2H), 5.41 (br s, 2H), 4.30 (s, 2H), 3.79 (s, 3H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customa brownish clear solution was obtained
  4. temperatureAfter 2 hours of reflux
  5. customthe solvent was removed in vacuo
  6. dissolutionThe obtained oil was dissolved with minimum amount of isopropanol
  7. customa yellow powder was precipitated by the addition of water

Sources & evidence

ORD record
ord-d4a8a4b70a8e4b178573405bc2348e94
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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