Lithium Hydroxide → 3-Chloro-4-formyl-1H-pyrrole-2-carboxylic acid

HRID 1874957Notes

Reaction equation

HRID 1874957 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[C:8]([CH:9]=[O:10])=[CH:7][NH:6][C:5]=1[C:11]([O:13]C)=[O:12]>C1COCC1.CO>[Cl:3][C:4]1[C:8]([CH:9]=[O:10])=[CH:7][NH:6][C:5]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86644899Methyl 3-chloro-4-formyl-1H-pyrrole-2-carboxylate

Product 1

HCID 866449013-Chloro-4-formyl-1H-pyrrole-2-carboxylic acidYield 84.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1 N in water, 2 mL, 2 mmol) was added to a solution of methyl 3-chloro-4-formyl-1H-pyrrole-2-carboxylate (0.050 g, 0.26 mmol) in THF (2 mL) and methanol (2 mL). The solution was stirred at RT overnight. The solvents were evaporated to afford a residue which was partitioned between EtOAc and 1 N HCl. The organic layer was separated, dried over MgSO4, filtered and evaporated to a solid to afford the title compound (0.038 g, 83%) as a crude product which was used with no further purification. 1H NMR (400 MHz, Acetone-d6) δ ppm 11.76 (br. s., 1H), 9.90 (s, 1H), 7.72 (d, 1H). LCMS: m/z=174.2 (M+1).

Workup

  1. customThe solvents were evaporated
  2. customto afford a residue which
  3. customwas partitioned between EtOAc and 1 N HCl
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to a solid

Sources & evidence

ORD record
ord-b0b8259cdef542a08974b53032145aba
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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