Dimethylformamide → 6-Quinolinecarbaldehyde

HRID 2080029Notes

Reaction equation

HRID 2080029 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2.CN(C)[CH:19]=[O:20].[Cl-].[NH4+]>C(OCC)C>[N:13]1[C:14]2[C:9](=[CH:8][C:7]([CH:19]=[O:20])=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 792436-BromoquinolineHCID 178418339Butyllithium

Product 1

HCID 7656536-QuinolinecarbaldehydeYield 8.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

n-Butyl lithium (19.2 mL; 1.5M hexane solution) was added dropwise to a solution of 6-bromoquinoline (5 g, 24.0 mmol) in diethyl ether (20 mL) that had been cooled to −70° C. under nitrogen atmosphere, a solution of N,N-dimethylformamide (3.7 mL, 48.0 mmol) in diethyl ether was further added, and the solution was stirred at −70° C. for 2 hours. The reaction solution was allowed to room temperature, then, an aqueous solution of saturated ammonium chloride was added, the solution was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and the title compound (320 mg, 8.5%) was obtained as a yellow oil.

Workup

  1. customwas allowed to room temperature
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-5dc3a094eb4242d8bba6b0ce19d0fd9b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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