Ethanol → HCID 178506146, compound

HRID 1524699Notes

Reaction equation

HRID 1524699 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=O.C(O)C.[NH2:21]N>>[F:14][C:13]([F:16])([F:15])[C:9]1[CH:8]=[C:7]([C:5]2[CH:4]=[CH:3][NH:2][N:21]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 5398493(2E)-3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]prop-2-en-1-one

Product 1

HCID 178506146HCID 178506146, compoundYield 90.6%

Procedure

The (2E)-3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]prop-2-en-1-one (0.32 g, 0.0013 mol) was dissolved in ethanol (10.0 mL, 0.171 mol) and hydrazine (0.24 mL, 0.0078 mol) under nitrogen and heated to reflux. The reaction was monitored by HPLC and was complete almost immediately. The mixture was allowed to cool to rt and concentrated to give the crude product as an oil. The product was purified by FCC on silica gel eluting with a hexane: ethyl acetate gradient to give 3-[3-(trifluoromethyl)phenyl]-1H-pyrazole as an oil (0.25 g, 89%), LC/MS (M+H)+: 213, 1H NMR (CDCl3) δ 8.06 (s, 1H), 7.99 (d, 1H, J=7.5), 7.66 (d, 1H, J=2.4), 7.57 (m, 1H), 7.55 (d, 1H, J=7.5), 6.69 (d, 1H, J=2.4).

Workup

  1. concentrationconcentrated
  2. customto give the crude product as an oil
  3. customThe product was purified by FCC on silica gel eluting with a hexane

Sources & evidence

ORD record
ord-4934278e07ce47a8981aba0a370447f8
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Reaction notes

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