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

HRID 655754Notes

Reaction equation

HRID 655754 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 15) 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. The combined EtOAc layers were dried over anhydrous MgSO4, filtered and the solvent was removed to give 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. dry with materialThe combined EtOAc layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-a2e2600c47784d9d83e36584ef40b6d7
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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