Hexane → (3-Ethoxy-4-methoxy-phenyl)-quinolin-6-yl-methanone

HRID 2377134Notes

Reaction equation

HRID 2377134 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.CCCCCC.CON(C)[C:27]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:28]>C1COCC1.O.C(O)(C)C>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([C:27]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][CH:33]=[CH:32]3)=[O:28])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH3:12]

Participants

8

Reactant 4

HCID 8058HexaneHCID 217726904-Bromo-2-ethoxy-1-methoxybenzeneHCID 55211172N-Methoxy-N-methylquinoline-6-carboxamideHCID 178418339Butyllithium

Product 1

HCID 68938696(3-Ethoxy-4-methoxy-phenyl)-quinolin-6-yl-methanoneYield 67.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-2-ethoxy-1-methoxy-benzene (1.74 g, 7.5 mmol) in THF (15 mL) was added a solution of n-butyllitium in hexane (3.0 mL, 2.5 N, 7.5 mmol) at −78° C. and kept for 20 min. To the mixture was added a solution of quinoline-6-carboxylic acid methoxy-methyl-amide (1.55 g, 7.2 mmol) in THF (10 mL) at −78° C. After 2 h, isopropanol (2 mL) and water (50 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The solvent was removed and the residue was stirred with ether (20 mL). Filtration gave (3-ethoxy-4-methoxy-phenyl)-quinolin-6-yl-methanone as a yellow solid (1.5 g). The solid was used in the next step without further purification.

Workup

  1. waitAfter 2 h
  2. customthe cold bath was removed
  3. customThe solvent was removed
  4. stirringthe residue was stirred with ether (20 mL)
  5. filtrationFiltration

Sources & evidence

ORD record
ord-82732451f01142cb97f37b03d0f97d9a
Source dataset
uspto-grants-2008_12
Patent number
US07468446B2

Reaction notes

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