Sodium Hydroxide → 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acid

HRID 1948350Notes

Reaction equation

HRID 1948350 reaction equation
[Cl:1][C:2]1[C:3]([C:13]#[N:14])=[C:4]([C:8]([O:10]CC)=[O:9])[NH:5][C:6]=1[CH3:7].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[C:3]([C:13]#[N:14])=[C:4]([C:8]([OH:10])=[O:9])[NH:5][C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66707683ethyl 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylate2×

Product 1

HCID 594025744-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acidYield 90.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 670 mg (3.2 mmol) of ethyl 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylate (Intermediate 193) and 3.2 ml (3.2 mmol) 1N NaOH in 20 ml MeOH was heated at 100° C. in a microwave reactor for 2 h. The mixture was diluted with water and extracted with EtOAc. The EtOAc was washed with 1N NaOH. The combined aqueous layers were acidified with concentrated HCl and extracted 2 times with EtOAc, each extract being washed with brine. Drying (MgSO4) and removal of solvent gave 535 mg of product as a solid. MS (ES) (M−H−): 183 for C7H5ClN2O2; NMR (d6-DMSO): 2.2 (s, 3H), 12.9 (s, 1H), 13.3 (s, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc was washed with 1N NaOH
  3. extractionextracted 2 times with EtOAc
  4. washeach extract being washed with brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-d0cf9f87f81a4d89bf77774d8885c384
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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