3,4-Dimethylaniline → HCID 21938025, compound

HRID 1393548Notes

Reaction equation

HRID 1393548 reaction equation
F[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[CH3:20])[NH2:16]>ClCCl>[CH3:12][C:13]1[CH:14]=[C:15]([NH:16][C:2]2[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:18][C:19]=1[CH3:20]

Participants

4

Reactant 2

HCID 72483,4-DimethylanilineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 21938025HCID 21938025, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

3 g of 3-fluoro-4-nitrophenol and 6.9 g of 3,4-dimethylaniline were mixed and stirred for 2 hours at 150° C. After cooling, it was dissolved in dichloromethane and extracted six times with 1N aqueous hydrochloric acid. The organic phase was discarded, and the combined aqueous phases were extracted three times with chloroform. The combined extracts were dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was chromatographed on silica gel.

Workup

  1. temperatureAfter cooling
  2. extractionextracted six times with 1N aqueous hydrochloric acid
  3. extractionthe combined aqueous phases were extracted three times with chloroform
  4. customThe combined extracts were dried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-1cf45f7b9a274d9abbd30ee535f9a510
Source dataset
uspto-grants-2008_03
Patent number
US07345075B2

Reaction notes

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