2-Methyl-4-methoxyaniline → HCID 22177895, compound

HRID 2373314Notes

Reaction equation

HRID 2373314 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].O.[C:12]1(C)[CH:17]=CC(S(O)(=O)=O)=[CH:14][CH:13]=1.[C:23](#[N:27])[CH2:24][C:25]#[N:26]>C1(C)C=CC=CC=1.OC(C)C(=O)C>[NH2:26][C:25]1[N:4]([C:3]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:2]=2[CH3:1])[C:13]([CH3:14])=[C:12]([CH3:17])[C:24]=1[C:23]#[N:27]

Participants

6

Reactant 3

HCID 76102-Methyl-4-methoxyanilineHCID 8010MalononitrileHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 22177895HCID 22177895, compound

Reagents, catalysts & solvents 2

HCID 179AcetoinSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-methyl-4-methoxyaniline (10 g) in toluene (120 ml), acetoin and p-toluenesulfonic acid hydrate (44 mg) were added. The mixture was refluxed with heating for 2 hours. After the reaction mixture was cooled to room temperature, malononitrile (4.6 ml) was added to the reaction mixture, and it was refluxed with heating for 12 hours. The cooled reaction mixture was concentrated. The residue was diluted with ether, and filtered to give the title compound (5.73 g) having the following physical data

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. temperaturewas refluxed
  4. temperaturewith heating for 12 hours
  5. customThe cooled reaction mixture
  6. concentrationwas concentrated
  7. additionThe residue was diluted with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-404062bf8085454b997b96219fcfabbf
Source dataset
uspto-grants-2008_12
Patent number
US07459459B2

Reaction notes

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