Methyl chloroformate → 6-Methoxy-2-(3-methoxyphenyl)quinoline

HRID 1827947Notes

Reaction equation

HRID 1827947 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([O-])=[CH:8][CH:7]=[CH:6]2.ClC(OC)=O.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([Mg]Br)[CH:24]=[CH:25][CH:26]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([O:20][CH3:19])[CH:26]=1)[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 2538216-Methoxyquinoline N-oxideHCID 178490745HCID 178490745, compound

Product 1

HCID 220646106-Methoxy-2-(3-methoxyphenyl)quinolineYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-methoxyquinoline-N-oxide (175 mg, 1.0 mmol) in THF (3 mL) at room temperature is added methyl chloroformate (77 uL, 1.0 mmol). The mixture is cooled to 0° C. and 3-methoxyphenylmagnesium bromide (2 mL of 1M, 2 mmol) is added dropwise. The mixture is stirred for 16 h while warming to room temperature. The solvent is removed in vacuo and the resulting residue is partitioned between water and CH2Cl2. The organic phase is washed with water and brine, dried over MgSO4, filtered and concentrated. Flash chromotography (0–20% EtOAc/hexanes) yields 6-methoxy-2-(3-methoxy-phenyl)-quinoline (123 mg, 46% yield).

Workup

  1. temperaturewhile warming to room temperature
  2. customThe solvent is removed in vacuo
  3. customthe resulting residue is partitioned between water and CH2Cl2
  4. washThe organic phase is washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8c25b71552ab4600b5e5ddfe561eb5d8
Source dataset
uspto-grants-2006_06
Patent number
US07056931B2

Reaction notes

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