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

HRID 1740739Notes

Reaction equation

HRID 1740739 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-f618e473f3b14bf39e9caef259c7829c
Source dataset
uspto-grants-1999_10
Patent number
US05972930

Reaction notes

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