2-(3-Methyl-2,2'-bipyridin-6-yl)isoindoline-1,3-dione → 3-Methyl-2,2'-bipyridin-6-amine

HRID 1890743Notes

Reaction equation

HRID 1890743 reaction equation
[CH3:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:4][C:5]([N:8]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:6][CH:7]=1>C(O)C.C(N)CN>[CH3:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 583179152-(3-Methyl-2,2'-bipyridin-6-yl)isoindoline-1,3-dione

Product 1

HCID 583180113-Methyl-2,2'-bipyridin-6-amine

Reagents, catalysts & solvents 2

HCID 3301EthylenediamineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(3-methyl-2,2′-bipyridin-6-yl)isoindoline-1,3-dione (129 mg, 0.41 mmol) in ethanol (2 ml) is added a couple of drops of ethylenediamine at room temperature. The solution is stirred at room temperature for 30 minutes. The solvents are removed by rotary evaporation and the crude product is purified by silica gel flash chromatography, eluted with 3% methanol in dichloromethane to afford 3-methyl-2,2′-bipyridin-6-amine as an off-white solid. LC-MS m/z: 186.1 (M+1).

Workup

  1. customThe solvents are removed by rotary evaporation
  2. customthe crude product is purified by silica gel flash chromatography
  3. washeluted with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-09e716a1deee478e8eedc157bbcca1a7
Source dataset
uspto-grants-2013_08
Patent number
US08507491B2

Reaction notes

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