Sodium Hydroxide → 1-Methyl-4-nitropyrrole-2-carboxylic acid

HRID 1776664Notes

Reaction equation

HRID 1776664 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=[C:3]1[C:10]([O:12]C)=[O:11].[OH-].[Na+]>C1COCC1.O.O>[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=[C:3]1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2759930Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

Product 1

HCID 27369151-Methyl-4-nitropyrrole-2-carboxylic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate (5.0 g, 27.17 mmol) in 120 ml of 1:1 THF/H2O was added 8 g of NaOH in 30 ml of water. The mixture was stirred overnight, concentrated, diluted with water, extracted with EtAc/Hexane (1:1). The aqueous solution was adjusted to pH 3˜4 with 20% H3PO4 and extracted with EtAc (4×60 ml). The organic solutions were combined, dried over MgSO4, filtered, evaporated and crystallized with ethanol/EtAc/Hexane to afford 4.06 g (88%) of the title product. 1H NMR (DMSO) 13.12 (s, 1H), 8.21 (s, 1H), 7.25 (s, 1H), 3.91 (s, 3H); 13C NMR 160.97, 134.01, 129.16, 123.81, 111.38, 37.47; MS m/z−169.1 (M−H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with EtAc/Hexane (1:1)
  4. extractionextracted with EtAc (4×60 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customcrystallized with ethanol/EtAc/Hexane

Sources & evidence

ORD record
ord-eb9975b1f0e741ecbcd79cd3e7b8ea92
Source dataset
uspto-grants-2016_02
Patent number
US09265841B2

Reaction notes

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