Benzoylhydrazine → HCID 11253605, compound

HRID 900054Notes

Reaction equation

HRID 900054 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, compound

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) title 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)

Sources & evidence

ORD record
ord-39343359fef849f5bc376dd03a8444af
Source dataset
uspto-grants-2008_04
Patent number
US07358238B2

Reaction notes

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