Hydrochloric Acid → 3-chloro-1H-pyrrole-2-carboxylic acid

HRID 1874843Notes

Reaction equation

HRID 1874843 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:8]=[CH:7][NH:6][C:5]=1[C:9]([O:11]C)=[O:10].C1COCC1.Cl>CO>[Cl:3][C:4]1[CH:8]=[CH:7][NH:6][C:5]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 5324605Methyl 3-chloro-1H-pyrrole-2-carboxylate

Product 1

HCID 221800183-chloro-1H-pyrrole-2-carboxylic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1M LiOH (7.415 ml, 7.415 mmole) was added to methyl 3-chloro-1H-pyrrole-2-carboxylate (0.2958 g, 1.854 mmole) dissolved in methanol (4 ml). To the solution was added THF (4 ml) and the resulting mixture was heated to 60° C. for 4 h. The mixture was acidified with 1M HCl and partitioned with EtOAc. The organic phase was dried over MgSO4 and evaporated to afford the title compound (0.2331 g, 86%) as a brownish solid. 1H NMR (400 MHz, Acetone-d6): δ ppm 11.01 (br. s., 1H), 7.03 (t, 1H), 6.23 (t, 1H). MS: m/z 146.2 (M+1).

Workup

  1. custompartitioned with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-8550914d4eb340c09669b03ce62b97f1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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