Hexane → 4-Chlorobenzo[4,5]furo[3,2-b]pyridine-3 carbonitrile

HRID 989330Notes

Reaction equation

HRID 989330 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:3]=12.CCCCCC.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:3]=12

Participants

4

Reactant 3

HCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 178510324HCID 178510324, compound

Product 1

HCID 98993994-Chlorobenzo[4,5]furo[3,2-b]pyridine-3 carbonitrileYield 65%

Procedure

A mixture of 2.10 g (11.0 mmol) of 4-hydroxybenzo[4,5]furo[3,2-b]pyridine-3-carbonitrile in 15 mL of phosphorous oxychloride is heated at reflux temperature for 1.5 hours, then cooled to room temperature. Hexane is added and the solid is collected by filtration, dissolved in ethyl acetate and washed with cold 1 N NaOH. The organic layer is dried over sodium sulfate, filtered through a pad of diatomaceous earth and concentrated in vacuo to give 1.55 g (65%) of a red solid, mp 229-231° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1.5 hours
  3. filtrationthe solid is collected by filtration
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with cold 1 N NaOH
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered through a pad of diatomaceous earth
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cea3a8cf1fca4b28ac01349593d4ee87
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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