Carbon Dioxide → HCID 67323561, compound

HRID 2365433Notes

Reaction equation

HRID 2365433 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.C([Li:17])CCC.[C:18](=[O:20])=[O:19]>C1COCC1>[CH3:12][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([C:18]([O-:20])=[O:19])=[CH:3][CH:4]=2)[N:9]=1.[Li+:17]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 123328967-Bromo-2-methylquinolineHCID 178418339Butyllithium

Product 1

HCID 67323561HCID 67323561, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 7-bromo-2-methylquinoline (400 mg, supplier Bioblocks Inc.) in THF (8 mL) under argon at −78° C. was added n-butyllithium (0.865 mL) dropwise. The reaction was stirred for 15 minutes at −78° C. before it was poured onto solid carbon dioxide in a beaker. The mixture was swirled until warmed to room temperature to prevent bumping, then the solvent was removed in vacuo to give the crude title compound (404 mg), which was used directly in subsequent reactions.

Workup

  1. temperatureuntil warmed to room temperature
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-70f84bcc30c24ab3a3c1744636c0fec8
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

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