3-Chloroaniline → HCID 23289827, compound

HRID 366396Notes

Reaction equation

HRID 366396 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].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:3]=[C:4]([NH:5][C:10]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:15]#[N:16])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 79323-ChloroanilineHCID 98930Cyclopentanecarbonitrile, 2-oxo-HCID 5284359Calcium Chloride

Product 1

HCID 23289827HCID 23289827, compound

Procedure

3-Chloro-aniline (Aldrich Chemicals) (5.1 g, 40.0 mmol), cyano-ketone (Example 11) (4.4 g, 40.4 mmol) and calcium chloride (5.0 g, 45.0 mmol) in T.H.F. (60 ml) were heated under reflux for 17 hours. After cooling, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (150° C., 0.2 mmHg) gave the product as light yellow powder.

Workup

  1. temperature(60 ml) were heated
  2. temperatureunder reflux for 17 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe solvent evaporated
  6. distillationKugelrohr distillation (150° C., 0.2 mmHg)

Sources & evidence

ORD record
ord-168d8f3b5474467f9bbc3b0a28c1b27c
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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