Hydrochloric Acid → 4,5-Dichloro-1H-pyrrole-2-carboxylic acid

HRID 2233854Notes

Reaction equation

HRID 2233854 reaction equation
[OH-].[Li+].O.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]([O:13]CC)=[O:12])[NH:8][C:9]=1[Cl:10].Cl>C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]([OH:13])=[O:12])[NH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68580104Ethyl 4,5-dichloro-1H-pyrrole-2-carboxylate2×

Product 1

HCID 162274944,5-Dichloro-1H-pyrrole-2-carboxylic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of lithium hydroxide in water (2 N, 0.80 ml, 0.16 mol) was added to a stirred solution of a mixture of ethyl 4,5-dichloro-1H-pyrrole-2-carboxylate (Intermediate 59; 7.0 g, 0.033 mol) in THF (15 ml) at room temperature. The mixture was stirred at 50° C. for 8 h over 2 days. The reaction mixture was acidified with 10% HCl solution to a pH ˜2 and partitioned between EtOAc and water. The organic layer was dried over MgSO4 and concentrated in vacuo to give the title compound (4.0 g).

Workup

  1. custompartitioned between EtOAc and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ca8f833f99c4a22a45efa2d2120dc92
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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