Hydrochloric Acid → HCID 17938112, compound

HRID 2117726Notes

Reaction equation

HRID 2117726 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-8408f59812de401ab59795b5cae2061a
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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