Methanol → 3-Cyanobenzohydrazide

HRID 732127Notes

Reaction equation

HRID 732127 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[N:2].CO.[NH2:14][NH2:15]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:14][NH2:15])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 219426583-CyanobenzohydrazideYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-cyanobenzoyl chloride (4.8 g, 29.0 mmol) was dissolved in DCM (20 ml) and MeOH (40 ml) was added in portions at 0° C. The mixture was stirred at 0° C. for 1 h and at rt for 2 h. The solvents were evaporated and the crude methyl ester was dissolved in EtOH (50 ml) and hydrazine (24% aq., 9 ml, 45 mmol) was added. The reaction mixture was refluxed for 48 h and the solvents were evaporated (coevaporation with water). The residue was purified with prep. HPLC to give the title compound (1.8 g, 39%). 1H NMR (DMSO-d6): 9.98 (br s, 1 H), 8.21 (m, 1 H), 8.13 (m, 1 H), 7.99 (m, 1 H), 7.69 (t, 1 H), 4.61 (br s, 2 H).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe crude methyl ester was dissolved in EtOH (50 ml)
  3. temperatureThe reaction mixture was refluxed for 48 h
  4. customthe solvents were evaporated (coevaporation with water)
  5. customThe residue was purified with prep

Sources & evidence

ORD record
ord-3207d49b5089412e9f4edf21dc4ec507
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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