Potassium Iodide → HCID 67301095, compound

HRID 1015424Notes

Reaction equation

[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[I-].[K+].[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH3:20][N:21]1[CH2:25][CH2:24][CH2:23][C:22]1=O>>[C:1]1([O:11][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:17][C:14]2[CH:10]=[CH:1][CH:2]=[C:22]3[C:23]=2[CH:24]=[CH:25][CH:20]=[N:21]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 70051-Naphthol

HCID 11430Potassium Carbonate

HCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 67301095HCID 67301095, compoundYield 86%

Conditions

Temperature: 90 °C

Procedure

The above-obtained compound (1.06 g, 3.62 mmol) was suspended together with 1-naphthol (521 mg, 3.62 mmol) and potassium iodide (60 mg, 0.36 mmol) in N-methylpyrrolidinone (10 mL). To the suspension, potassium carbonate (0.75 g, 5.42 mmol) was added. After stirred at 90° C. for 4 h, the reaction mixture was quenched with water (30 mL) followed by extraction with ethyl acetate (30 mL×3). The organic layers were combined, washed with brine, and concentrated under vacuum. The residue was purified by silica gel chromatography to give 5-[5-(naphthalen-1-yloxy)-pentyloxy]-quinoline (1.11 g, 3.11 mmol, 86%) as a white solid.

Workup

customthe reaction mixture was quenched with water (30 mL)
extractionfollowed by extraction with ethyl acetate (30 mL×3)
washwashed with brine
concentrationconcentrated under vacuum
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-c58dc826ba244d1aaf931856e57ea876
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985763B2

Reaction notes

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