Pyridine → 4-(3-Methoxy-phenyl)-1-(1-pyridin-2-yl-2-quinolin-4-yl-ethylideneamino)-pyrrolidin-2-one

HRID 8229Notes

Reaction equation

HRID 8229 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=O)[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.N1C=CC=CC=1.[NH2:26][N:27]1[CH2:31][CH:30]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=2)[CH2:29][C:28]1=[O:40]>C(O)(=O)C>[CH3:39][O:38][C:34]1[CH:33]=[C:32]([CH:30]2[CH2:31][N:27]([N:26]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:8][C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=[CH:11][CH:10]=3)[C:28](=[O:40])[CH2:29]2)[CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 109338561-(Pyridin-2-yl)-2-(quinolin-4-yl)ethanoneHCID 219926971-Amino-4-(3-methoxy-phenyl)-pyrrolidin-2-one

Product 1

HCID 865926244-(3-Methoxy-phenyl)-1-(1-pyridin-2-yl-2-quinolin-4-yl-ethylideneamino)-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-pyridin-2-yl-2-quinolin-4-yl-ethanone, (0.25 g, 1 mmol) and pyridine (0.242 mL, 3 mmol) in acetic acid (2 mL) is added to 1-amino-4-(3-methoxy-phenyl)-pyrrolidin-2-one, (0.2 g, 1 mmol) at room temperature under nitrogen. The mixture is stirred 18 h and concentrated in vacuo. The residue is chromatographed on SiO2 (2% methanol/dichloromethane) to yield the title compound, 0.25 g (57%), as a yellow foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is chromatographed on SiO2 (2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b641563e84c94560b4b6dd88498fa0b5
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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