Hydrazine → 3-(Pyridin-2-yl)propan-1-amine

HRID 915655Notes

Reaction equation

HRID 915655 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O.NN>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][NH2:10]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 16640922HCID 16640922, compound

Product 1

HCID 31596143-(Pyridin-2-yl)propan-1-amineYield 129.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Place 2-(3-pyridin-2-yl-propyl)isoindole-1,3-dione (7.0 g, 26.0 mmol) in a flask and add a solution of hydrazine (4.0 mL) in MeOH (200 mL). After 12 hours, filter the mixture and concentrate the filtrate, titrate with methylene chloride, and filter a second time. Perform flash chromatography on silica gel eluting with 80:18:2 CHCl3/MeOH/concentrated NH4OH to afford the title compound as a brown oil (4.59 g) MS: m/e=137 (MH+).

Workup

  1. filtrationfilter the mixture
  2. concentrationconcentrate the filtrate
  3. filtrationtitrate with methylene chloride, and filter a second time

Sources & evidence

ORD record
ord-3878d723f32b48c7b22ee9d9e9b4df09
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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