8-Hydroxy-5,6,7,8-tetrahydro-quinoline-3-carbonitrile synthesis

4synthesis methods

Product Name:8-Hydroxy-5,6,7,8-tetrahydro-quinoline-3-carbonitrile
CAS Number:1400683-17-1
Molecular formula:C10H10N2O
Molecular Weight:174.2

3-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-, 1-oxide

1400683-16-0
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8-Hydroxy-5,6,7,8-tetrahydro-quinoline-3-carbonitrile

1400683-17-1
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Yield:1400683-17-1 87.1%

Reaction Conditions:

Stage #1: 3-cyano-5,6,7,8-tetrahydroquinoline 1-oxidewith trifluoroacetic anhydride in acetic acid at 23; for 18 h;Cooling;
Stage #2: with sodium hydroxide in water;acetic acid; for 0.5 h;

Steps:

c

c) 8-Hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile To a solution of 3-cyano-5,6,7,8-tetrahydroquinoline 1-oxide (645 mg, 3.7 mmol) was added dropwise under ice cooling trifluoroacetic anhydride (6.22 g, 4.18 ml, 29.6 mmol). The light yellow solution was stirred at 23° C. for 18 h. The mixture was quenched with 1 N NaOH solution and stirred vigorously for 30 min., then extracted twice with dichloromethane, the combined organic layers were dried over Na₂SO₄, filtered and evaporated. The residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 8-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (562 mg, 3.23 mmol, 87.1% yield) as a white solid. MS (ISP): m/z=175.1 [(M+H)⁺].

References:

US2012/238548,2012,A1 Location in patent:Page/Page column 41

8-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile

1400683-18-2
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1400683-17-1
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References

5,6,7,8-tetrahydro-3-quinolinecarbonitrile

101871-76-5
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1400683-17-1
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References

65242-27-5 Synthesis

2-CHLORO-5,6,7,8-TETRAHYDROQUINOLINE-3-CARBONITRILE

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1400683-17-1
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References