Hydrochloric Acid → HCID 17938112, compound

HRID 852311Notes

Reaction equation

HRID 852311 reaction equation
[Na].[C:2](OCC)(=O)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=1.Cl>O.C(O)C>[C:21]([CH:20]([C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=1)[CH2:2][C:3]1[CH:4]=[CH:5][N:6]=[CH:7][CH:8]=1)#[N:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15291Ethyl isonicotinateHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 5360545Sodium

Product 1

HCID 17938112HCID 17938112, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

250 ml of dry ethanol were added dropwise to metallic sodium (17.3 g/0.7 mol). Ethyl isonicotinate (75.8 g/0.5 mol) and 4-fluorophenylacetonitrile (67.6 g/0.5 mol) were then added dropwise, and the mixture was subsequently heated under reflux for 15 min. After cooling, 600 ml of distilled water were added to the mixture. When the mixture was acidified to pH 1 using concentrated hydrochloric acid (HCl), the desired compound 2-cyano-2-(4-fluorophenyl)-1-(4-pyridyl)ethane precipitated as a yellow precipitate. The precipitate was filtered off, washed with distilled water and dried under reduced pressure over phosphorus pentoxide (P2O5). The yield was 85.0 g (62%).

Workup

  1. temperaturethe mixture was subsequently heated
  2. temperatureunder reflux for 15 min
  3. temperatureAfter cooling
  4. customthe desired compound 2-cyano-2-(4-fluorophenyl)-1-(4-pyridyl)ethane precipitated as a yellow precipitate
  5. filtrationThe precipitate was filtered off
  6. washwashed with distilled water
  7. dry with materialdried under reduced pressure over phosphorus pentoxide (P2O5)

Sources & evidence

ORD record
ord-799c050fce9c4bdb841d1859a0d028a6
Source dataset
uspto-grants-2007_08
Patent number
US07253191B2

Reaction notes

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