Hydrazine hydrate (1:1) → 6-(3-aminopropoxy)-1-methyl-1H-quinolin-2-one

HRID 69000Notes

Reaction equation

HRID 69000 reaction equation
O.NN.[CH3:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:30]>C(O)C>[NH2:19][CH2:18][CH2:17][CH2:16][O:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:5]([CH3:4])[C:6](=[O:30])[CH:7]=[CH:8]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 669605512-[3-(1-Methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]isoindole-1,3-dione

Product 1

HCID 669605486-(3-aminopropoxy)-1-methyl-1H-quinolin-2-oneYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (6.54 ml) was added to a ethanol solution (250 ml) of 2-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]isoindole-1,3-dione (16.28 g), and stirred while heating under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure. A 1N-sodium hydroxide aqueous solution was added to the residue, and stirred for 30 minutes, and extraction with dichloromethane was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution, in this order. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (8.04 g) as a colorless oil.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionA 1N-sodium hydroxide aqueous solution was added to the residue
  5. stirringstirred for 30 minutes
  6. extractionextraction with dichloromethane
  7. washThe organic layer was washed with water
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3e504be718d4f08a710a9c3cf965a34
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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