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

HRID 1505055Notes

Reaction equation

HRID 1505055 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-1ca986cc5714491da23f00cd84ad41b4
Source dataset
uspto-grants-2015_12
Patent number
US09216964B2

Reaction notes

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