4-Bromoaniline → SMR000102306

HRID 366394Notes

Reaction equation

HRID 366394 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[C:15]#[N:16].[Cl-].[Ca+2].[Cl-]>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:15]#[N:16])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 98930Cyclopentanecarbonitrile, 2-oxo-HCID 5284359Calcium Chloride

Product 1

HCID 622051SMR000102306

Procedure

4-Bromo-aniline (Aldrich Chemicals) (3.5 g, 20 mmol), cyano-ketone (Example 11) (2.2 g, 20 mmol), calcium chloride (2.5 g, 23 mmol) and T.H.F. (30 ml) were heated under reflux for 7 hours. After being allowed to cool, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (150° C., 0.07 mmHg) gave the product as a brown-grey powder.

Workup

  1. temperature(30 ml) were heated
  2. temperatureunder reflux for 7 hours
  3. temperatureto cool
  4. filtrationthe mixture was filtered
  5. customthe solvent evaporated
  6. distillationKugelrohr distillation (150° C., 0.07 mmHg)

Sources & evidence

ORD record
ord-d147e446509947a89d08c958616866ce
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

Loading…