Sodium Hydroxide → HCID 58488523, compound

HRID 451367Notes

Reaction equation

HRID 451367 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[C:10]=1[CH3:18].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([C:14]([OH:16])=[O:15])[C:10]=1[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58488518methyl 5-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 58488523HCID 58488523, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 5-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate (0.64 g, 2.4 mmol) in methanol (10 ml) was added 5N NaOH (10 ml) and the mixture was stirred at 80° C. for 4.0 h. The reaction mixture was concentrated on a rotary evaporator. To the residue was added water and washed with Et2O. The resulting solution was neutralized with conc HCl and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over sodium sulfate and concentrated on a rotary evaporator to give the title compound (610 mg, quant) as a brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated on a rotary evaporator
  2. additionTo the residue was added water
  3. washwashed with Et2O
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-c1c84ca280644972b23e69b4f3753b2c
Source dataset
uspto-grants-2013_07
Patent number
US08487117B2

Reaction notes

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