Water → HCID 23510412, compound

HRID 1883176Notes

Reaction equation

HRID 1883176 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9].O.[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[N:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=[C:5]([CH2:6][N:3]2[CH:7]=[CH:6][CH:5]=[C:4]2[CH:8]=[O:9])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 13854Pyrrole-2-carboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 23510412HCID 23510412, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 60% NaH (3.28 g) in THF (400 ml) was cooled to 0° C. under nitrogen atmosphere, and thereto was added pyrrol-2-carbaldehyde (7.81 g) in portions. To the mixture was added a solution of the above crude bromo compound in toluene, and the mixture was stirred at room temperature for 0.5 hour, and stirred at 40° C. for one hour, and further stirred at 50° C. for 2 hours. The mixture was cooled to room temperature, and poured into water, and extracted with ethyl acetate. The extract was washed with a saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=3/1→2/1→1/1) to give 1-(3-quinolylmethyl)-1H-pyrrol-2-carbaldehyde (10.5 g, 54%).

Workup

  1. stirringstirred at 40° C. for one hour
  2. stirringfurther stirred at 50° C. for 2 hours
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column (hexane/ethyl acetate=3/1→2/1→1/1)

Sources & evidence

ORD record
ord-5a04fd1a777a40dbb2e376ae4cf0f8d8
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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