1-Chloro-4-nitrobenzene → Methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate

HRID 365608Notes

Reaction equation

HRID 365608 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([O:10][CH3:11])=[O:9].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 103992Methyl 1-methylpyrrol-2-acetate

Product 1

HCID 23285895Methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetateYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 1-methylpyrrole-2-acetate (5.0 g, 32.0 mmol) and 4-chloronitrobenzene (10.3 g, 65.0 mmol) were dissolved in DMF (30 ml) and the mixture was cooled in an ice bath under argon. Sodium hydride, 50% in mineral oil, (3.1 g, 64.0 mmol) was added in portions. After stirring for 1 h at room temperature the reaction mixture was poured into 1 M HCl/ice and the product was extracted into ethyl acetate. The organic extracts were washed with water, dried over sodium sulfate, and concentrated to dryness. Purification on a Florisil® column (methylene chloride) gave methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate (4.13 g, 46%) as a solid. ##STR38##

Workup

  1. temperaturethe mixture was cooled in an ice bath under argon
  2. extractionthe product was extracted into ethyl acetate
  3. washThe organic extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification on a Florisil® column (methylene chloride)

Sources & evidence

ORD record
ord-fa6f667e9afa445bac4dc54403728451
Source dataset
uspto-grants-2000_10
Patent number
US06127402

Reaction notes

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