Ethanol → HCID 67266806, compound

HRID 598146Notes

Reaction equation

HRID 598146 reaction equation
[C:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[CH3:16])[C:4]=1[C:17](OCC)=O)#[N:2].[OH2:22].[NH2:23][NH2:24].C(O)C>O>[NH2:2][C:1]1[C:3]2[CH:7]=[CH:6][N:5]([C:8]3[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=3[CH3:16])[C:4]=2[C:17](=[O:22])[NH:23][N:24]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)2×HCID 67267520HCID 67267520, compound

Product 1

HCID 67266806HCID 67266806, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-cyano-1-mesityl-1H-pyrrole-2-carboxylate (0.5 g, 1.77 mmol), hydrazine monohydrate (0.86 ml, 17.7 mmol) and ethanol (20 ml) was heated under reflux for 2 days. During the reaction, additional hydrazine monohydrate (0.86 ml×2) was added. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (50 ml×2). The extracts were combined, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with dichloromethane/ethyl acetate (3:1-1:1) to give 297 mg (63%) of the title compound as crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. additionwas added
  4. extractionextracted with ethyl acetate (50 ml×2)
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with dichloromethane/ethyl acetate (3:1-1:1)

Sources & evidence

ORD record
ord-0d4d45542b924ea8b3e2b6c8bdedc864
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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