Hydrazine hydrate (1:1) → HCID 135508237, compound

HRID 2369831Notes

Reaction equation

HRID 2369831 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]2[CH:6]=[C:7]([C:9](=O)[CH2:10][C:11](=O)/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:8][C:4]=2[CH:3]=1.O.[NH2:25][NH2:26]>C(O)(=O)C.C(O)C>[C:14]1(/[CH:13]=[CH:12]/[C:11]2[NH:26][N:25]=[C:9]([C:7]3[O:8][C:4]4[CH:3]=[C:2]([OH:1])[CH:23]=[CH:22][C:5]=4[CH:6]=3)[CH:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59028462HCID 59028462, compound

Product 1

HCID 135508237HCID 135508237, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
382.5 °C

Procedure

To a mixture of (4E)-1-(6-hydroxy-1-benzofuran-2-yl)-5-phenylpent-4-ene-1,3-dione (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 65-700° C. overnight. The solvent was removed under reduced pressure to afford crude product. The crude product was purified by reverse phase HPLC. The fractions from HPLC were combined, neutralized with 1.0 N aqueous sodium hydroxide solution, and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford the product (11% yield): 1H NMR (400 MHz, CD3Cl): δ 7.58 (br d, 2H), 7.35 (m, 4H), 7.25 (t, 2H), 7.10 (br d, 1H), 7.05 (br s, 1H), 6.94 (br d, 1H), 6.88 (br s, 1H), 6.75 (dd, 1H); MS (EI) for C19H14N2O2: 303 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford crude product
  3. customThe crude product was purified by reverse phase HPLC
  4. additiondiluted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7bbf47c5a6664d69a9c4302ca29e6e87
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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