p-Toluenesulfonic acid → HCID 17917423, compound

HRID 1387663Notes

Reaction equation

HRID 1387663 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:11][N:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 67351-IndanoneHCID 7515N-Methylaniline

Product 1

HCID 17917423HCID 17917423, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a dry flask equipped with a Dean-Stark trap and a reflux condenser were placed 1-indanone (10.0 g, 75.7 mmol). N-methylaniline (15.1 g, 141 mmol) and toluene (200 mL). A catalytic amount of p-toluenesulfonic acid (0.1 g) was added and the mixture was refluxed under N2 for 96 hours. The reaction was cooled and the toluene was removed under reduced pressure before the remaining material was distilled under vacuum. The highest boiling fraction (6.8 g; bp 150-2° C./0.7 mm Hg) was collected as a yellow oil which solidified to a yellow-orange solid on standing. This material was stored in a glove box. Analysis by NMR indicated ca. 10 percent N-methylaniline in the product. However, further distillation on another sample of distilled enamine was not successful in lowering the amount of unwanted amine in the product.

Workup

  1. customInto a dry flask equipped with a Dean-Stark trap and a reflux condenser
  2. temperaturethe mixture was refluxed under N2 for 96 hours
  3. temperatureThe reaction was cooled
  4. customthe toluene was removed under reduced pressure before the remaining material
  5. distillationwas distilled under vacuum
  6. customThe highest boiling fraction (6.8 g; bp 150-2° C./0.7 mm Hg) was collected as a yellow oil which
  7. customThis material was stored in a glove box
  8. distillationHowever, further distillation on another sample of distilled enamine

Sources & evidence

ORD record
ord-07acca8efd044551adbe15080ef4e0be
Source dataset
uspto-grants-2001_07
Patent number
US06268444B1

Reaction notes

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