Hydrochloric Acid → HCID 69661060, compound

HRID 2303433Notes

Reaction equation

HRID 2303433 reaction equation
[Na].[C:2]([O:10]CC)(=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.[O-]CC.[ClH:26]>O.C(O)C>[ClH:26].[C:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=1)=[C:2]([C:3]1[CH:4]=[CH:5][N:6]=[CH:7][CH:8]=1)[OH:10])#[N:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 15291Ethyl isonicotinateHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 1194401-Hydroxyethyl radicalHCID 5360545Sodium

Product 1

HCID 69661060HCID 69661060, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

17.3 g (0.75 mol) of metallic sodium were treated dropwise with 250 ml of absolute ethanol. 75.8 g (0.5 mol) of ethyl isonicotinate and 67.6 g (0.5 mol) of 4-fluorophenylacetonitrile were added to the ethoxide. The reaction mixture was stirred at 100° C. for 15 min. The mixture was then cooled in an ice bath and treated with 600 ml of dist. water. On acidifying to pH 1 using 90 ml of conc. HCl, the title compound deposited as a yellow precipitate. The precipitate was filtered off, washed with dist. water and dried over P2O5 in vacuo. Yield: 85.0 g (62%).

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. additiontreated with 600 ml of dist

Sources & evidence

ORD record
ord-5af0d70047aa4b42af2759aba2a75a2f
Source dataset
uspto-grants-2002_08
Patent number
US06432988B1

Reaction notes

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