4-Chloroaniline → HCID 612513, compound

HRID 366388Notes

Reaction equation

HRID 366388 reaction equation
[Cl: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-]>>[Cl: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 78124-ChloroanilineHCID 98930Cyclopentanecarbonitrile, 2-oxo-HCID 5284359Calcium Chloride

Product 1

HCID 612513HCID 612513, compound

Procedure

4-Chloro-aniline (Aldrich Chemicals) (2.6 g, 20 mmol), cyanoketone (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 19 hours. After being allowed to cool, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (160° C., 0.3 mm Hg) gave the product as white crystals.

Workup

  1. temperature(30 ml) were heated
  2. temperatureunder reflux for 19 hours
  3. temperatureto cool
  4. filtrationthe mixture was filtered
  5. customthe solvent evaporated
  6. distillationKugelrohr distillation (160° C., 0.3 mm Hg)

Sources & evidence

ORD record
ord-0e8119df54f74cc3bb3bd44bc430cdf6
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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