Water → Quinoline

HRID 1392129Notes

Reaction equation

HRID 1392129 reaction equation
[N+:1]1([O-])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClC(OCC(C)C)=O.C([Mg]Br)=C.O>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15366Quinoline 1-oxideHCID 62365Isobutyl chloroformateHCID 178418507HCID 178418507, compound

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

0.8 g (5.51 mmol) of quinoline N-oxide is dissolved in 15 ml of anhydrous THF at 20° C., in a dry round-bottomed flask equipped with a magnetic stirrer and a nitrogen inlet. This solution is treated with 0.78 ml (6.07 mmol) of isobutyl chloroformate; the suspension obtained is cooled to −78° C. 11 ml (11 mmol) of a 1M solution of vinylmagnesium bromide in THF are then added dropwise. After stirring for 90 minutes at −78° C., the solution is slowly returned to ambient temperature (30 minutes), and then hydrolyzed with 15 ml of water.

Workup

  1. customequipped with a magnetic stirrer and a nitrogen inlet
  2. customthe suspension obtained
  3. customis slowly returned to ambient temperature
  4. custom(30 minutes)

Sources & evidence

ORD record
ord-9c00a5e60cfd4236a1474d201653dbf4
Source dataset
uspto-grants-2008_03
Patent number
US07342026B2

Reaction notes

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