Nitrogen → HCID 17797188, compound

HRID 2287355Notes

Reaction equation

HRID 2287355 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11](=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N#N.[CH2:23]([Mg]Br)[CH3:24].COC(C)(C)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11]([CH2:23][CH3:24])([OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 947NitrogenHCID 15413tert-Butyl methyl etherHCID 23433474tert-Butyl 7-methoxy-4-oxo-3,4-dihydroquinoline-1(2H)-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 17797188HCID 17797188, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a flame dried 250 mL round bottom flask equipped with a magnetic stir bar and a N2 gas inlet was added IV (2.23 mg, 8.05 mmol) in dry THF (100 mL). The solution was cooled to 0° C. under a blanket of N2 and a 1.0M solution of ethyl magnesium bromide (EtMgBr) in methyl-tert-butyl ether (16.1 mL, 16.1 mmol, 2 equiv) was added via syringe. The solution was stirred at 0° C. for 1 h. The reaction was quenched with NH4Cl (saturated aqueous solution) extracted with EtOAc, dried (MgSO4), and concentrated to give V as a colorless oil (1.11 g, 3.61 mmol, 45%). Spectral data matched that previously disclosed for this compound.

Workup

  1. customTo a flame dried 250 mL round bottom flask
  2. customequipped with a magnetic stir bar and a N2 gas inlet
  3. customThe reaction was quenched with NH4Cl (saturated aqueous solution)
  4. extractionextracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e6d4baf56cfe4d998acfb62a08a5982a
Source dataset
uspto-grants-2000_07
Patent number
US06083956

Reaction notes

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