Lithium Hydroxide → 5-(Aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylic acid

HRID 1874968Notes

Reaction equation

HRID 1874968 reaction equation
[Li+].[OH-].[NH2:3][C:4]([C:6]1[NH:10][C:9]([C:11]([O:13]C)=[O:12])=[C:8]([Cl:15])[CH:7]=1)=[O:5]>C1COCC1.CO>[NH2:3][C:4]([C:6]1[NH:10][C:9]([C:11]([OH:13])=[O:12])=[C:8]([Cl:15])[CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68481017Methyl 5-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylate

Product 1

HCID 684804915-(Aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylic acidYield 101.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1 N in water, 2 mL, 2 mmol) was added to a solution of methyl 5-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylate (0.0602 g, 0.297 mmol) in THF (2 mL) and methanol (2 mL) and the solution was stirred at RT overnight. The reaction mixture was evaporated to a residue and partitioned with EtOAc and 1 N HCl. The organic layer was separated, dried over MgSO4 and evaporated to a solid to afford the title compound (0.057 g, 77%) as a tan solid which was used with no further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.07 (br. s., 1H), 7.80 (br. s., 1H), 7.43 (br. s., 1H), 6.57-6.89 (m, 1H).

Workup

  1. customThe reaction mixture was evaporated to a residue
  2. custompartitioned with EtOAc and 1 N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated to a solid

Sources & evidence

ORD record
ord-0363c8686f144e87b79f1bc915ca6fc0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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