Benzoylhydrazine → HCID 11253605, compound

HRID 2239237Notes

Reaction equation

HRID 2239237 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:12]([NH:20][NH2:21])(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[C:13]1([C:12]2[N:3]3[CH:4]=[CH:5][C:6]4[C:11]([C:2]3=[N:21][N:20]=2)=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 11955BenzoylhydrazineHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 11253605HCID 11253605, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-chloro-isoquinoline (4 g, 24.45 mmol) in ethanol (50 ml) was added benzoic acid hydrazide (4 g, 29.34 mmol) and the mixture was stirred at reflux temperature for 16 hrs. The reaction mixture was cooled and the precipitate was filtered off and recrystallised from ethanol (50 ml) affording 1.9 g of impure (NMR) tile compound. The filtrate was purified by silicagel chromatography using a mixture of ethyl acetate/heptane (1:2) as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 0.2 g (3%) of the title compound as a solid.

Workup

  1. temperatureat reflux temperature for 16 hrs
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe precipitate was filtered off
  4. customrecrystallised from ethanol (50 ml)
  5. customaffording 1.9 g of impure (NMR) tile compound
  6. customThe filtrate was purified by silicagel chromatography
  7. additiona mixture of ethyl acetate/heptane (1:2) as eluent
  8. customPure fractions were collected
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9c4210217e2a45ab80c6ab3c5a3c2c34
Source dataset
uspto-grants-2010_05
Patent number
US07723323B2

Reaction notes

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