1,2-Dimethoxyethane → HCID 53755971, compound

HRID 1012047Notes

Reaction equation

HRID 1012047 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([CH2:10]OC)OC.Br[C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2>C(Cl)(Cl)Cl>[C:23]1([C:14]2[CH:15]=[N:16][C:19]3[C:7]([CH:10]=2)=[CH:21][CH:22]=[CH:17][CH:18]=3)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:15]=[CH:14][CH:23]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 214133-Bromoquinoline

Product 1

HCID 53755971HCID 53755971, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

Next, 1.0 mL of 2.0 M potassium carbonate aqueous solution and tris(triphenylphosphine)palladium [Pd(PPh3)4] (30 mg, 0.026 mmol) were added to 4 mL of dimethoxyethane (DME) solution of the 1-naphthylboronic acid ester (2-1) (1.00 g, 5.00 mmol) and 3-bromoquinoline (0.62 g, 3.00 mmol), which then was refluxed at 90° C. for 12 hours. After completion of the reaction, it was cooled to room temperature, and 100 mL of chloroform was added thereto. This was washed with 100 mL of water twice and subsequently was washed with 50 mL of saturated saline. The solvent was removed therefrom and this then was purified by column chromatography using chloroform as a developing solvent. Thus 3-(1-naphthyl)quinoline (2-2) was obtained (84 mg, 11%). The instrumental analysis data of this 3-(1-naphthyl)quinoline (2-2) is indicated below.

Workup

  1. customAfter completion of the reaction, it
  2. temperaturewas cooled to room temperature
  3. washThis was washed with 100 mL of water twice
  4. washsubsequently was washed with 50 mL of saturated saline
  5. customThe solvent was removed
  6. customthis then was purified by column chromatography

Sources & evidence

ORD record
ord-21252dbf870e418b8223f7684999d967
Source dataset
uspto-grants-2011_07
Patent number
US07977486B2

Reaction notes

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