1-Methylpyrrole → HCID 22461848, compound

HRID 1936518Notes

Reaction equation

HRID 1936518 reaction equation
[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[CH:5]=[CH:6][CH:7]=[N:8][C:9]=2[C:10](=[O:12])[CH:11]=1.[CH3:14][N:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1>C(O)(=O)C>[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[CH:5]=[CH:6][CH:7]=[N:8][C:9]=2[C:10](=[O:12])[C:11]=1[C:16]1[N:15]([CH3:14])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 73041-MethylpyrroleHCID 13029628HCID 13029628, compound

Product 1

HCID 22461848HCID 22461848, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.58 mmol of 6-chloroquinoline-5,8-dione with 20.7 mmol of 1-methylpyrrole in 50 ml of acetic acid is stirred at room temperature for 24 hours. The medium is subsequently concentrated under reduced pressure, the residue is extracted with chloroform and the combined organic phases are washed in succession with aqueous sodium carbonate solution and then water before being dried over magnesium sulphate, filtered and concentrated under vacuum. The crude product obtained is purified by chromatography on a silica gel column to give 6-chloro-7-(1-methyl-1H-pyrrol-2-yl)quinoline-5,8-dione with a yield of 40%.

Workup

  1. concentrationThe medium is subsequently concentrated under reduced pressure
  2. extractionthe residue is extracted with chloroform
  3. washthe combined organic phases are washed in succession with aqueous sodium carbonate solution
  4. dry with materialwater before being dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product obtained
  8. customis purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-beec6873da92417fae80dfb234134463
Source dataset
uspto-grants-2002_05
Patent number
US06391064B1

Reaction notes

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