Water → Quinoline

HRID 1392131Notes

Reaction equation

HRID 1392131 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.C([Mg]Br)(C)C.O.[CH2:14]1[CH2:18]O[CH2:16][CH2:15]1>>[N:2]1[C:3]2[C:4](=[CH:18][CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][CH:1]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 13387N-methyl-2-pyrrolidoneHCID 178418365HCID 178418365, compound

Product 1

HCID 7047Quinoline

Procedure

0.2 g (6.38×10−4 mol) of 1,1-dibromo-2-(2-quinolyl)ethene obtained from 2-formylquinoline, carbon tetrabromide (CBr4) and triphenylphosphine (PPh3) (Ramirez et al., J. Am. Chem. Soc., 1962, 84: 1745) and 11.28 mg (3.19×10−5 mol, 5 mol %) of iron triacetylacetonate (Fe(acac)3) are dissolved in 3 ml of anhydrous THF and 3 ml of anhydrous N-methylpyrrolidone (NMP) at −10° C., in a dry round-bottomed flask equipped with a magnetic stirrer and a nitrogen inlet. 0.39 ml (7.02×10−4 mol) of a 1.8M solution of isopropyl magnesium bromide in THF is added dropwise to the solution. After stirring for 30 minutes, the reaction is hydrolyzed with 10 ml of water and the solution is brought back to ambient temperature. Next, the two phases are separated and the aqueous phase is extracted with diethyl ether (3×30 ml).

Workup

  1. customis brought back to ambient temperature
  2. customNext, the two phases are separated
  3. extractionthe aqueous phase is extracted with diethyl ether (3×30 ml)

Sources & evidence

ORD record
ord-6be23b6f12af41fba18279207dd34c54
Source dataset
uspto-grants-2008_03
Patent number
US07342026B2

Reaction notes

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