Hydrazine → 3-(Pyridin-4-yl)propan-1-amine

HRID 915658Notes

Reaction equation

HRID 915658 reaction equation
NN.[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1>CO>[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 12015796N-[3-(4-Pyridyl)propyl]phthalimide

Product 1

HCID 143474663-(Pyridin-4-yl)propan-1-amineYield 83.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add a solution of hydrazine (4.0 mL) in methanol (200 mL) to 2-(3-pyridin-4-yl-propyl)isoindole-1,3-dione (8.0 g, 30 mmol). After 48 hours, filter the mixture and concentrate the filtrate, triturate with methylene chloride (150 mL), and filter a second time. Perform the filtrate via flash chromatography on silica gel eluting with 80:18:2 CHCl3/MeOH/concentrated NH4OH) to afford the title compound as a yellow oil (3.42 g). MS: m/e=137 (MH+).

Workup

  1. filtrationfilter the mixture
  2. concentrationconcentrate the filtrate
  3. customtriturate with methylene chloride (150 mL)
  4. filtrationfilter a second time

Sources & evidence

ORD record
ord-9d83af56edac480782a45cec3a471834
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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