Thionyl Chloride → 3-Hydroxynaphthalene-2-carbonitrile

HRID 356986Notes

Reaction equation

HRID 356986 reaction equation
C([O:4][C:5]1[C:6]([C:15]([NH2:17])=O)=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(=O)C.S(Cl)(Cl)=O>>[OH:4][C:5]1[C:6]([C:15]#[N:17])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 18936915HCID 18936915, compound

Product 1

HCID 129902643-Hydroxynaphthalene-2-carbonitrileYield 66%

Procedure

A mixture of 19 (4.96 g, 21.6 mmol) and thionyl chloride (6.32 ml, 86.4 mmol) was heated under reflux for 2 hours. The solution was concentrated in vacuo to dryness. The residue was taken up in water (10 ml), methanol (200 ml) and 1N NaOH solution (75 ml). The solution was stirred at room temperature for 19 hours and concentrated. Chromatography, eluting with 1:1 cyclohexane/ethyl acetate, provided 2.41 g (66%) of 20 as yellow crystals, mp 188°-189° C. (lit. mp 188°-189° C.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe solution was concentrated in vacuo to dryness
  4. concentrationconcentrated
  5. washChromatography, eluting with 1:1 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-0dbeaabbd07e42f8b58841d4fed27806
Source dataset
uspto-grants-1998_11
Patent number
US05840739

Reaction notes

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