Hydrazine hydrate (1:1) → HCID 57834058, compound

HRID 730028Notes

Reaction equation

HRID 730028 reaction equation
[C:1]1([CH:11]([N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:12])[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:3][CH:2]=1.O.NN>C(O)C>[C:1]1([CH:11]([NH2:13])[CH3:12])[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68814169HCID 68814169, compound

Product 1

HCID 57834058HCID 57834058, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

2-[1-(Azulen-1-yl)ethyl]-isoindole-1,3-dione (16.8 g) prepared in Example 72, Step B was dissolved in ethanol (400 mL), added with hydrazine monohydrate (3.1 g, Wako Pure Chemical Industries), and stirred at 30° C. for 72 hours. The solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was added with saturated aqueous sodium hydrogencarbonate, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel chromatography (NH-DM1020, Fuji Silysia, hexane:ethyl acetate=3:1-1:1) to obtain 9.26 g of the title compound.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was added with saturated aqueous sodium hydrogencarbonate
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by NH silica gel chromatography (NH-DM1020, Fuji Silysia, hexane:ethyl acetate=3:1-1:1)

Sources & evidence

ORD record
ord-a8a211bc0b134580a4b29348545f38b7
Source dataset
uspto-grants-2009_09
Patent number
US07582658B2

Reaction notes

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