Hydrazine hydrate (1:1) → 2-(6-Methoxypyridin-2-yl)ethan-1-amine

HRID 2202232Notes

Reaction equation

HRID 2202232 reaction equation
O.NN.[CH3:4][O:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:9]=[CH:8][CH:7]=1>CCO>[CH3:4][O:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][NH2:14])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 153198721H-Isoindole-1,3(2H)-dione, 2-[2-(6-methoxy-2-pyridinyl)ethyl]-

Product 1

HCID 212435192-(6-Methoxypyridin-2-yl)ethan-1-amineYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (24.94 mL, 514.18 mmol) was added to a solution of 2-(2-(6-methoxypyridin-2-yl)ethyl)isoindoline-1,3-dione (29.03 g, 102.84 mmol) in EtOH (300 mL) at room temperature. The mixture was heated under reflux for 1 hr, and allowed to be cooled to room temperature. The insoluble substance was removed by filtration, and washed with a mixed solvent of diethyl ether/IPE (1:1). The filtrate was concentrated under reduced pressure, and to the obtained residue was added toluene (about 250 mL), and the mixture was concentrated again under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, solvent gradient; 10→100% ethyl acetate/hexane) to give 2-(6-methoxypyridin-2-yl)ethanamine (14.43 g, 95 mmol, 92%) as a colorless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customThe insoluble substance was removed by filtration
  4. washwashed with a mixed solvent of diethyl ether/IPE (1:1)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionto the obtained residue was added toluene (about 250 mL)
  7. concentrationthe mixture was concentrated again under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (NH, solvent gradient; 10→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4a0acc98e7294123bfbc45c7aba82037
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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