Hydrazine hydrate (1:1) → HCID 178488694, compound

HRID 1475941Notes

Reaction equation

HRID 1475941 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]#[N:12])=[CH:5][CH:4]=1.O.[NH2:15][NH2:16]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([NH2:12])[NH:16][N:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2333984-Methoxybenzoylacetonitrile

Product 1

HCID 178488694HCID 178488694, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(4-methoxyphenyl)-3-oxopropanenitrile (5.0 g, 28.5 mmol) in ethanol (100 mL) was added hydrazine hydrate (2.8 mL, 57.1 mmol) at room temperature. The mixture was heated to reflux for 8 h, allowed to cool and concentrated under reduced pressure to about ¼ volume (25 mL). The resulting precipitate was allowed to stir overnight at room temperature, filtered and rinsed with ethanol (2 mL). The title product was dried under vacuum. Yield 4.15 g (77%); LCMS m/z 190.1 (M+H)+, ret. time=1.56 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 h
  3. temperatureto cool
  4. concentrationconcentrated under reduced pressure to about ¼ volume (25 mL)
  5. filtrationfiltered
  6. washrinsed with ethanol (2 mL)
  7. dry with materialThe title product was dried under vacuum

Sources & evidence

ORD record
ord-715a7a7de92f433e802d3035a0ecd1f3
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

Loading…