Ethanol → HCID 178509693, compound

HRID 1524701Notes

Reaction equation

HRID 1524701 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])=O.C(O)C.[NH2:19]N>>[NH:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[N:19]1

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 57140731-(3-Cyanophenyl)-3-(dimethylamino)acrolein

Product 1

HCID 178509693HCID 178509693, compoundYield 84.7%

Procedure

The 3-[(2E)-3-(dimethylamino)prop-2-enoyl]benzonitrile (0.600 g, 0.00300 mol) was dissolved in ethanol (20.0 mL, 0.342 mol) and hydrazine (0.56 mL, 0.018 mol) under an atmosphere of nitrogen was stirred at room temperature for 1.5 h. The reaction was concentrated in vacuo to give a dark product which was purified by FCC on silica gel, eluting with ethyl acetate-hexane 1:1 to give 3-(1H-pyrazol-3-yl)benzonitrile as an oil (0.430 g, 84%), LC/MS (M+H)+: 170.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto give a dark product which
  3. customwas purified by FCC on silica gel
  4. washeluting with ethyl acetate-hexane 1:1

Sources & evidence

ORD record
ord-77ac4f5923b74e12a39b9c478a767ec4
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Reaction notes

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