Ethanol → HCID 178509693, compound

HRID 1501428Notes

Reaction equation

HRID 1501428 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-3c75800d635b499d806bf7565923a01c
Source dataset
uspto-grants-2015_12
Patent number
US09206187B2

Reaction notes

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