4-Methoxyphenylhydrazine hydrochloride → HCID 67196817, compound

HRID 1013020Notes

Reaction equation

HRID 1013020 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3](=O)[CH2:4][C:5](=O)[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][NH2:28])=[CH:23][CH:22]=1>C(O)C.O>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:5]([CH:6]=[CH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:4][C:3]([C:2]([F:17])([F:16])[F:1])=[N:28]2)=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 2853017HCID 2853017, compound

Product 1

HCID 67196817HCID 67196817, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1,1,1-Trifluoro-6-phenylhex-5-ene-2,4-dione (2.28 mmol) and 4-methoxyphenylhydrazine hydrochloride (435 mg, 2.5 mmol) were heated in ethanol (7 mL) at 70° C. overnight. The solution was diluted with water and extracted with ethyl acetate. The ethyl acetate extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine, then dried over MgSO4 and concentrated. SiO2 chromatography with 5-20% ethyl acetate/hexanes gave 0.14 g of the desired product, along with many mixed fractions. Only the clean fractions were carried on. LC-MS (C19H15F3N2O calculated 344) m/z 345 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.43-7.30 (m, 7H), 7.12 (d, J=16.2 Hz, 1H), 7.05-7.00 (m, 2H), 6.88 (s, 1H), 6.78 (d, J=16.2 Hz, 1H), 3.89 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d40682082ba34bfe8656d41bb74c17b8
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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