Methane, dichloromethoxy- → 7-Methoxy-1,2,4,5-tetrahydroimidazo[1,2-a]quinoline-8-carboxaldehyde

HRID 1856776Notes

Reaction equation

HRID 1856776 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[CH2:13][CH2:14][N:15]=[C:8]1[CH2:7][CH2:6]2.[CH:16]([O:19]C)(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:16]=[O:19])[N:9]1[CH2:13][CH2:14][N:15]=[C:8]1[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 221329127-Methoxy-1,2,4,5-tetrahydroimidazo[1,2-a]quinoline

Product 1

HCID 221329197-Methoxy-1,2,4,5-tetrahydroimidazo[1,2-a]quinoline-8-carboxaldehydeYield 35%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Compound 14 (63 mg, 0.31 mmol) in CH2Cl2 (5 ml) was added TiCl4 (0.17 ml, 1.6 mmol) at 0° C. After the reaction mixture was stirred for 10 minutes, Cl2CHOMe (0.14 ml, 1.6 mmol) was added at 0° C., and stirred for 3 h. The mixture was quenched by the addition of water, basified with NaOH aq., and extracted with CH2Cl2. The combined CH2Cl2 extracts were dried over MgSO4, filtered, and concentrated. The residue was purified by SiO2 chromatography to give Compound 15 (25 mg, 35%) as a slight yellow solid.

Workup

  1. stirringstirred for 3 h
  2. customThe mixture was quenched by the addition of water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined CH2Cl2 extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-d6ff935e6dc94776803ebba41d7f4563
Source dataset
uspto-grants-2000_11
Patent number
US06143767

Reaction notes

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