Hexane → HCID 68935565, compound

HRID 2377135Notes

Reaction equation

HRID 2377135 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.C([Li])CCC.CCCCCC.CON(C)[C:26]([C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[CH:31]2)=[O:27]>C1COCC1.O>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([C:26]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[N:34]=[CH:33][CH:32]=[CH:31]3)=[O:27])[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 55211172N-Methoxy-N-methylquinoline-6-carboxamideHCID 178418339Butyllithium

Product 1

HCID 68935565HCID 68935565, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-3,5-dimethoxy-benzene (2.7 g, 12 mmol) in THF (20 mL) was added a solution of n-butyllitium in hexane (4.5 mL, 2.5 N, 11 mmol) at −78° C. and kept for 20 min. To the mixture was added quinoline-6-carboxylic acid methoxy-methyl-amide (2.2 g, 10 mmol) at −78° C. After 2 h, water (30 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers was washed with sodium hydrogen carbonate (50 mL, sat), brine (50 mL) and dried over magnesium sulfate. Removal of solvent and slurry in ether gave (3,5-dimethoxy-phenyl)-quinolin-6-yl-methanone as a white solid (1.48 g, 50% crude yield). The sample was used in the next step without further purification. 1H NMR (CDCl3) δ 3.84 (s, 6H, 2CH3), 6.70-6.73 (m, 1H, Ar), 6.97 (d, J=2 Hz, 1H, Ar), 7.49 (dd, J=4, 8 Hz, 1H, Ar), 8.17-8.28 (m, 4H, Ar), 9.02-9.04 (m, 1H, Ar).

Workup

  1. waitAfter 2 h
  2. customthe cold bath was removed
  3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers was washed with sodium hydrogen carbonate (50 mL, sat), brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent and slurry in ether

Sources & evidence

ORD record
ord-92650f9afe254f5bbf380cfd9a058541
Source dataset
uspto-grants-2008_12
Patent number
US07468446B2

Reaction notes

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