3,4,5-Trimethoxyaniline → HCID 21937998, compound

HRID 1393554Notes

Reaction equation

HRID 1393554 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][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[NH2:17]>C(OCC)(=O)C>[CH3:24][O:23][C:19]1[CH:18]=[C:16]([NH:17][C:2]2[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[CH:15]=[C:14]([O:13][CH3:12])[C:20]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 21937998HCID 21937998, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

3.7 g of 3-fluoro-4-nitrophenol and 4.76 g of 3,4,5-trimethoxyaniline were mixed and stirred for 10 hours at 100° C. After cooling, it was taken up in ethyl acetate and water and extracted three times with ethyl acetate. The combined organic phases were extracted three times with 1N aqueous hydrochloric acid and once with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation to a very large extent in a vacuum. The product was digested with diisopropyl ether.

Workup

  1. temperatureAfter cooling
  2. extractionwater and extracted three times with ethyl acetate
  3. extractionThe combined organic phases were extracted three times with 1N aqueous hydrochloric acid
  4. dry with materialonce with saturated sodium chloride solution, dried on sodium sulfate
  5. concentrationconcentrated by evaporation to a very large extent in a vacuum

Sources & evidence

ORD record
ord-52cf6155d4e446dba9ce4ef38b925562
Source dataset
uspto-grants-2008_03
Patent number
US07345075B2

Reaction notes

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