2-(6-Bromoquinolin-4-yl)-1-(6-methylpyridin-2-yl)ethanone → 1-[2-(6-Bromo-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-ethylideneamino]-pyrrolidin-2-one

HRID 915530Notes

Reaction equation

HRID 915530 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=1)=O.Cl.[NH2:23][N:24]1[CH2:28][CH2:27][CH2:26][C:25]1=[O:29]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][C:13](=[N:23][N:24]1[CH2:28][CH2:27][CH2:26][C:25]1=[O:29])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=1

Participants

4

Reactant 2

HCID 179806022-(6-Bromoquinolin-4-yl)-1-(6-methylpyridin-2-yl)ethanoneHCID 219928451-Aminopyrrolidin-2-one hydrochloride

Product 1

HCID 589588261-[2-(6-Bromo-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-ethylideneamino]-pyrrolidin-2-oneYield 69.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Stir a mixture of 2-(6-bromo-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-ethanone (38.5 g, 113 mmol) and 1-aminopyrrolidinone hydrochloride (20 g, 147 mmol) in 115 mL pyridine at ambient temperature for 10 hours. Add about 50 g 4 Å unactivated sieves. Continue stirring an additional 13 h and add 10–15 g silica and filter the mixture through a 50 g silica plug. Elute the silica plug with 3 L ethyl acetate. Combine the filtrates and concentrate in vacuo. Collect the hydrazone precipitate by filtration and suction dry to yield 33.3 g (69.7%) of the desired subtitled intermediate as an off-white solid.

Workup

  1. additionAdd about 50 g 4 Å unactivated sieves
  2. stirringContinue stirring an additional 13 h
  3. additionadd 10–15 g silica
  4. filtrationfilter the mixture through a 50 g silica plug
  5. washElute the silica plug with 3 L ethyl acetate
  6. concentrationconcentrate in vacuo
  7. customCollect the hydrazone precipitate
  8. filtrationby filtration and suction
  9. customdry

Sources & evidence

ORD record
ord-5999024b150d4f038090fb7d3645261d
Source dataset
uspto-grants-2007_09
Patent number
US07265225B2

Reaction notes

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