Water → Quinoline

HRID 1392128Notes

Reaction equation

HRID 1392128 reaction equation
C([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)=O.C1(P(=CC=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1(C)C=CC=CC=1>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 796192-Quinolinecarboxaldehyde

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.2 g (1.27 mmol) of 2-formylquinoline is dissolved in 10 ml of anhydrous toluene, in a dry round-bottomed flask equipped with a magnetic stirrer and a nitrogen inlet. 0.46 g (1.52 mmol) of (triphenylphosphoranylidene)acetaldehyde is added to this solution. The mixture is brought back to the reflux temperature of toluene for 90 minutes, and the solution is then slowly brought back to ambient temperature and hydrolyzed with 10 ml of water. After separation of the two phases, the aqueous phase is extracted with ethyl acetate (4×50 ml).

Workup

  1. customequipped with a magnetic stirrer and a nitrogen inlet
  2. customAfter separation of the two phases
  3. extractionthe aqueous phase is extracted with ethyl acetate (4×50 ml)

Sources & evidence

ORD record
ord-e5faab79cb0d4274b7130ae8921c3bdc
Source dataset
uspto-grants-2008_03
Patent number
US07342026B2

Reaction notes

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