Lithium Hydroxide → 1-Methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acid

HRID 1776668Notes

Reaction equation

HRID 1776668 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:18])[CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:19]([O:21]C)=[O:20].[Li+].[OH-]>CC(N(C)C)=O.O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:18])[CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 592893Methyl 1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylate

Product 1

HCID 4041101-Methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Methyl 1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxylate (2.0 g, 6.53 mmol) in 50 ml of DMA was added 2 g of LiOH 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 4.0 with 20% H3PO4 to form precipitates. The precipitates were filtered, washed with water and dried over P2O5 with vacuum to afford 1.4 g (73%) of the title product. 1H NMR (DMF-d7) 10.34 (br, 1H), 8.17 (s, 1H), 7.62 (s, 1H), 7.51 (s, 1H), 7.00 (s, 1H), 4.09 (s, 1H), 3.91 (s, 1H); 13C NMR 158.47, 135.61, 129.11, 127.77, 123.65, 121.57, 121.50, 109.48, 108.52, 38.38, 37.05; MS m/z−291.0 (M−H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with EtAc/Hexane (1:1)
  4. customto form
  5. customprecipitates
  6. filtrationThe precipitates were filtered
  7. washwashed with water
  8. dry with materialdried over P2O5 with vacuum

Sources & evidence

ORD record
ord-bbc000021dbe436691ad4a5a0678c6f3
Source dataset
uspto-grants-2016_02
Patent number
US09265841B2

Reaction notes

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