Sodium Hydroxide → 2,5-Dimethyl-4-(2,5-dimethyl-1-pyrrolyl)aniline

HRID 2181590Notes

Reaction equation

HRID 2181590 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([NH:15]C(=O)C)=[C:10]([CH3:19])[CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[OH-].[Na+]>C(O)C>[CH3:19][C:10]1[CH:9]=[C:8]([N:3]2[C:4]([CH3:7])=[CH:5][CH:6]=[C:2]2[CH3:1])[C:13]([CH3:14])=[CH:12][C:11]=1[NH2:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22481234HCID 22481234, compound

Product 1

HCID 224812372,5-Dimethyl-4-(2,5-dimethyl-1-pyrrolyl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product from stage b) (0.6 g), aqueous sodium hydroxide solution (10 ml, 10%) and ethanol (30 ml) was heated under reflux for 24 hours. On cooling, the mixture was extracted with diethyl ether (x2). The combined diethyl ether extracts were water washed, dried (MgSO4) and concentrated to give a crude product. Filtration through silica gave the title product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureOn cooling
  4. extractionthe mixture was extracted with diethyl ether (x2)
  5. washwashed
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a crude product
  9. filtrationFiltration through silica

Sources & evidence

ORD record
ord-c7d53c8cf86f4000a84ead1eeacdae5b
Source dataset
uspto-grants-2005_05
Patent number
US06893650B1

Reaction notes

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