Water → 4-Chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-2-carboxylic acid

HRID 1874962Notes

Reaction equation

HRID 1874962 reaction equation
[O-][Mn](=O)(=O)=O.[K+].O.[Cl:8][C:9]1[CH:13]=[C:12]([CH:14]=[O:15])[NH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17].[OH:20]S([O-])=O.[Na+]>CC(C)=O.Cl>[Cl:8][C:9]1[CH:13]=[C:12]([C:14]([OH:20])=[O:15])[NH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 86644900methyl 3-chloro-5-formyl-1H-pyrrole-2-carboxylate

Product 1

HCID 684860074-Chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-2-carboxylic acidYield 82%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 313Hydrochloric AcidSolvent

Procedure

KMnO4 (2.53 g, 16.0 mmol) was dissolved in acetone and water and added dropwise over a 2 hr period to a solution of methyl 3-chloro-5-formyl-1H-pyrrole-2-carboxylate (1.50 g, 8.00 mmol) in acetone (250 mL). After stirring for 4 hr the solution was poured into a solution of NaHSO3 in 1N HCl. This was extracted with EtOAc and the organic layer was washed with water. The organic layer was dried over MgSO4 and evaporated to afford the title compound (1.33 g, 82%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.15 (br. s., 1H), 12.75 (br. s., 1H), 6.78 (d, 1H), 3.77 (s, 3 H). LCMS: m/z 203.9 (M+1).

Workup

  1. extractionThis was extracted with EtOAc
  2. washthe organic layer was washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-e2e7ccbcfda8417bb9077cba948c64a1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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