Thionyl Chloride → 3-Hydroxynaphthalene-2-carbonitrile
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]=2Participants
3
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
- temperaturewas heated
- temperatureunder reflux for 2 hours
- concentrationThe solution was concentrated in vacuo to dryness
- concentrationconcentrated
- 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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