Hydrazine hydrate (1:1) → HCID 11615362, compound

HRID 1471857Notes

Reaction equation

HRID 1471857 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9](=O)[CH2:10][CH2:11][CH:12]=[CH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:17][NH2:18]>C(O)C>[CH2:10]([C:9]1[NH:18][N:17]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1)[CH2:11][CH:12]=[CH2:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 142891781-Phenylhept-6-ene-1,3-dione

Product 1

HCID 11615362HCID 11615362, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-phenylhept-6-ene-1,3-dione (3 g, 14.83 mmol) in ethanol (50 mL) was added hydrazine hydrate (2.228 g, 44.5 mmol) at room temperature. The reaction was refluxed for 10 h, cooled to room temperature and concentrated under reduced pressure. The residue was extracted with ethyl acetate. The organic extract was dried over MgSO4 and concentrated under reduced pressure to give the title compound without further purification. LCMS m/z=199.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.65-2.78 (m, 2H), 4.01-4.12 (m, 2H), 4.83-4.95 (m, 2H), 5.82-5.93 (m, 1H), 6.42 (s, 1H), 7.23-7.82 (m, 5H), 12.6 (s, 1H).

Workup

  1. temperatureThe reaction was refluxed for 10 h
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07682e85bca24c23b265fd66477ec19a
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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