Hydrazine hydrate (1:1) → HCID 178507276, compound

HRID 2054407Notes

Reaction equation

HRID 2054407 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([CH2:6][C:7]#[N:8])=O.O.[NH2:14][NH2:15]>C(O)C>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]1[CH:6]=[C:7]([NH2:8])[NH:14][N:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27342012-Chlorobenzoylacetonitrile

Product 1

HCID 178507276HCID 178507276, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chlorobenzoylacetonitrile (15.9 g, 89 mmol) and hydrazine hydrate (8.9 g, 0.18 mol) in ethanol (2 ml) was heated at reflux for 22 hr. After cooling to room temperature, the reaction was concentrated, in vacuo. The residue was dissolved in ethyl acetate, washed with water and brine, dried (MgSO4), and concentrated, in vacuo, to a brown oil. Flash chromatography using 10% ethyl acetate in methylene chloride, changing to 5% methanol in methylene chloride as eluant afforded title product I-3A-9a (17.3 g, quantitative): +ESI MS (M+1) 194.2; 1H NMR (400 MHz, CD3OD) δ 7.60-7.25 (m, 4H), 5.99 (br s, 1H).

Workup

  1. temperatureat reflux for 22 hr
  2. concentrationthe reaction was concentrated, in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated, in vacuo, to a brown oil

Sources & evidence

ORD record
ord-925332c827a241b8981cb92ab033b0c7
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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