Hydrazine hydrate (1:1) → HCID 22175526, compound

HRID 1797476Notes

Reaction equation

HRID 1797476 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([CH2:14][N:15]1C(=O)C3C(=CC=CC=3)C1=O)=[C:5]2[O:26][CH3:27].O.NN.C(=O)([O-])O.[Na+]>C(O)C.O1CCCC1>[ClH:1].[NH2:15][CH2:14][C:6]1[N:7]([CH3:13])[C:8](=[O:12])[C:9]2[C:4]([C:5]=1[O:26][CH3:27])=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 22175272HCID 22175272, compound

Product 1

HCID 22175526HCID 22175526, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{(6-chloro-4-methoxy-2-methyl-1oxo-1,2-dihydro-3-isoquinolinyl)methyl}-1H-isoindole-1,3(2H)-dione (0.38 g, 1 mmol) in ethanol (10 ml) and tetrahydrofuran (10 ml) was added hydrazine monohydrate (0.14 ml, 3 mmol). The obtained mixture was refluxed under heating for 2 h. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added a solution of 4N hydrogen chloride in ethyl acetate (2 ml), and the precipitated crystals were recrystallized from methanol-diethyl ether to give 3-(aminomethyl)-6-chloro-4-methoxy-2-methyl-1(2H)-isoquinolinone hydrochloride (0.08 g, 28.6%) as crystals.

Workup

  1. temperatureThe obtained mixture was refluxed
  2. temperatureunder heating for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added a solution of 4N hydrogen chloride in ethyl acetate (2 ml)
  8. customthe precipitated crystals were recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-1b66d81bc48c4561bda6fd0754398df9
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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