4-Fluoroaniline → 2-(4'Fluorophenyl) aminocyclohex-1-ene-1-carbonitrile
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]#[N:17].[Cl-].[Ca+2].[Cl-]>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:16]#[N:17])=[CH:4][CH:3]=1Participants
4
Procedure
4-Fluoro-aniline (1.11 g, 10.0 mmol), cyano-ketone (Example 32) (1.25 g, 10.2 mmol), calcium chloride (1.5 g, 13.5 mmol) and T.H.F. (20 ml) were heated under reflux for 17 hours. After cooling, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (135° C., 0.08 mmHg) gave the product as a pale yellow powder.
Workup
- temperature(20 ml) were heated
- temperatureunder reflux for 17 hours
- temperatureAfter cooling
- filtrationthe mixture was filtered
- customthe solvent evaporated
- distillationKugelrohr distillation (135° C., 0.08 mmHg)
Sources & evidence
- ORD record
- ord-686a9c224c1149408ed9747acb345109
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130228
Reaction notes
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