Hydrazine → Isoquinoline-3-carbohydrazide

HRID 409748

Reaction equation

HRID 409748 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13]C)=O)[N:2]=1.[NH2:15][NH2:16]>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH:15][NH2:16])=[O:13])[N:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 725374Methyl 3-isoquinolinecarboxylate

Product 1

HCID 55263898Isoquinoline-3-carbohydrazideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl isoquinoline-3-carboxylate (10 g, 53.42 mmol) in ethanol (100 mL) was added hydrazine (17.1 g). The reaction mixture was refluxed for 30 min and concentrated under high vacuum to remove hydrazine. The resulting residue was triturated with ethanol (20 mL) to give isoquinoline-3-carbohydrazide (8.6 g, 86%). LRMS (M+H+) m/z 188.1.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. concentrationconcentrated under high vacuum
  3. customto remove hydrazine
  4. customThe resulting residue was triturated with ethanol (20 mL)

Sources & evidence

ORD record
ord-4011f0480f4e446aa3625771427965f9
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Linked notes

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