Hydrazine hydrate (1:1) → HCID 178489663, compound

HRID 2369827Notes

Reaction equation

HRID 2369827 reaction equation
O[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]=[CH:11][C:12](=O)[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O.[OH2:23].[NH2:24][NH2:25].FC(F)(F)C([O-])=O>C(O)(=O)C.C(O)C>[CH3:9][O:8][C:7]1[CH:2]=[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:25][N:24]=2)[CH:4]=[CH:5][C:6]=1[OH:23]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 84468TrifluoroacetateHCID 68810693HCID 68810693, compound

Product 1

HCID 178489663HCID 178489663, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
67.5 °C

Procedure

To a mixture of 5-(hydroxy-3-methoxy-phenyl)-1-phenyl-pent-4-ene-1,3-dione (0.14 g, 0.48 mmol) and hydrazine monohydrate (0.02 g, 0.48 mmol) were added ethanol (24 mL) and acetic acid (1 drop) in a sealed tube. The reaction was heated at 65-70° C. overnight. The solvent was removed under reduced pressure to afford crude product. Purification on triethylamine treated silica (1:1 hexanes/ethyl acetate) afforded a mixture of two products. Reverse phase HPLC purification afforded 2-(methyloxy)-4-[(E)-2-(5-phenyl-1H-pyrazol-3-yl)ethenyl]phenol (0.015 g, 10% yield) as trifluoroacetate salt: 1H NMR (400 MHz, CDCl3): δ 9.21 (br s, 2H), 7.78 (br s, 2H), 7.42 (m, 3H), 7.20 (br d, 1H), 6.94 (m, 6H), 3.92 (s, 3H); MS (EI) for C18H16N2O2: 293 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford crude product
  3. customPurification on triethylamine
  4. additiontreated silica (1:1 hexanes/ethyl acetate)
  5. customafforded
  6. additiona mixture of two products
  7. customReverse phase HPLC purification

Sources & evidence

ORD record
ord-f09e2cf041bc43ebba49dad743fff26c
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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