Water → methyl 2-chloro-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate

HRID 554210Notes

Reaction equation

HRID 554210 reaction equation
[C:1]([CH:3]([CH:8]([CH3:18])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=O)[C:4]([O:6][CH3:7])=[O:5])#[N:2].C(OCC)(=O)C.[ClH:25].O>C(OCC)(=O)C>[Cl:25][C:1]1[NH:2][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[C:8]([CH3:18])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 21866389Hydrogen chloride-ethyl acetateHCID 66924807Methyl 2-cyano-4-(2-fluorophenyl)-3-methyl-4-oxobutanoate

Product 1

HCID 66924695methyl 2-chloro-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-cyano-4-(2-fluorophenyl)-3-methyl-4-oxobutanoate (31.0 g) in ethyl acetate (30 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (150 mL), and the mixture was stirred at room temperature for 2 days. To the reaction mixture was added water (200 mL), and the mixture was extracted with ethyl acetate. The extract was washed with water (twice) and saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound as white crystals (yield 19.3 g, 58%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water (twice) and saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-52260424307148f8b1a18e4e309ea910
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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