Oxalic Acid → HCID 14154274, compound

HRID 621804Notes

Reaction equation

HRID 621804 reaction equation
[Br:1][C:2]1[C:3]([O:19][CH:20]([CH3:22])[CH3:21])=[C:4]([C:14]([O:16]CC)=[O:15])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1[Br:7].[OH-].[Na+].C(O)(=O)C(O)=O>CO>[Br:1][C:2]1[C:3]([O:19][CH:20]([CH3:22])[CH3:21])=[C:4]([C:14]([OH:16])=[O:15])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 21243568HCID 21243568, compound

Product 1

HCID 14154274HCID 14154274, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 4,5-dibromo-3-(1-methylethoxy)-1-phenyl-1H-pyrrole-2-carboxylate (3.0 g, 0.007 moles) is dissolved in methanol (40 mL), 2N NaOH (20 mL) is added and the mixture stirred and heated to reflux under nitrogen. After 2 hours the mixture is cooled, then stripped of methanol under reduced pressure. The residue is acidified with oxalic acid and the precipitate is filtered off, rinsed well with warm water, and dried to afford the pure product (2.6 g); mp 76° C. (dec).

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen
  3. temperatureAfter 2 hours the mixture is cooled
  4. filtrationthe precipitate is filtered off
  5. washrinsed well with warm water
  6. customdried

Sources & evidence

ORD record
ord-743ad778d78d47568aeb4346568bc117
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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