Ethanol → HCID 178509693, compound

HRID 1843501Notes

Reaction equation

HRID 1843501 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-5b98d1a0460b4ef6a2e3ea21838b20f9
Source dataset
uspto-grants-2015_02
Patent number
US08946245B2

Reaction notes

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