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

HRID 2090605Notes

Reaction equation

HRID 2090605 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. Water (200 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed twice with water, and then washed with 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 twice with water
  3. washwashed with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5efebb475e274b61b882950e7623d65a
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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