Water → Quinoline

HRID 1392130Notes

Reaction equation

HRID 1392130 reaction equation
[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CC.CC(C)([O-])C.[K+].C([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1)=O.O>C1(C)C=CC=CC=1.O1CCCC1>[N:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:40]=[CH:41][CH:32]=1

Participants

7

Reactant 4

HCID 962WaterHCID 796192-QuinolinecarboxaldehydeHCID 80374Propyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

4.90 g (12.7 mmol) of propyltriphenylphosphonium bromide are suspended in 15 ml of anhydrous toluene at 0° C., in a dry round-bottomed flask equipped with a magnetic stirrer and a nitrogen inlet, and then 1.71 g (15.2 mmol) of potassium tert-butoxide (tBuOK) are added. After stirring for 15 minutes, a solution at 0° C. containing 1 g (6.36 mol) of 2-formylquinoline in 10 ml of anhydrous tetrahydrofuran is added. The reaction mixture is brought to the reflux temperature of toluene for 90 minutes, and the solution is then slowly brought back to ambient temperature and hydrolyzed with 20 ml of water.

Workup

  1. customequipped with a magnetic stirrer and a nitrogen inlet
  2. additionis added

Sources & evidence

ORD record
ord-7c45dd03b71a412aa6451362dee392f2
Source dataset
uspto-grants-2008_03
Patent number
US07342026B2

Reaction notes

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