P-Anisidine → HCID 12930157, compound

HRID 1081473Notes

Reaction equation

HRID 1081473 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[CH3:14][O:15][C:16]1[CH:22]=[CH:21][C:19](N)=[CH:18][CH:17]=1.CC1C=CC(C)=C(C)C=1C>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][C:19]2[CH:21]=[CH:22][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 102631,2,3,4-TetramethylbenzeneHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 12930157HCID 12930157, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g of 4-chloro-1,2-dinitrobenzene, 6.5 g of 4-methoxyaniline and 16 g of 1,2,3,4-tetramethylbenzene is refluxed for 15 hours. After cooling, water is added, the mixture is extracted with AcOEt, washed with a 1N solution of HCl , with a 1N solution of NaOH and with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is taken up with iso ether, a gummy insoluble material is separated off and the filtrate is chromatographed on alumina using iso ether as the eluent to give 4.6 g of the expected product after crystallization from isopropanol. M.p.=98° C.

Workup

  1. temperatureis refluxed for 15 hours
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with AcOEt
  4. washwashed with a 1N solution of HCl , with a 1N solution of NaOH and with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customa gummy insoluble material is separated off
  8. customthe filtrate is chromatographed on alumina using iso ether as the eluent

Sources & evidence

ORD record
ord-74e70f0c8e1a4842b5a8b621e0bdd417
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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