Trimethylsilyl iodide → HCID 20183631, compound

HRID 255598Notes

Reaction equation

HRID 255598 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]2)=[C:8]([C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=1)=[O:5])C.C[Si](I)(C)C>C(Cl)(Cl)Cl>[C:17]([C:8]1[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15](=[O:16])[N:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13]2)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide3×HCID 156320743-ethoxycarbonyl-1-benzoyl-4H-quinolizin-4-one

Product 1

HCID 20183631HCID 20183631, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-ethoxycarbonyl-1-benzoyl-4H-quinolizin-4-one (2.14 g) in chloroform (65 ml) was added dropwise trimethylsilyliodide (1.04 ml) at 0° C. After stirring for 30 minutes at 0° C., trimethylsilyliodide (1.04 ml) was added. After stirring for hour at room temperature, trimethylsilyliodide (1.04 ml) was added. After stirring for 2 hours at room temperature, the reaction mixture was diluted with chloroform and washed with water. After drying over magnesium sulfate, the chloroform extract was filtered and concentrated. The precipitate was washed with a cold chloroform to give 1-benzoyl-4H-quinolizin-4-one-3-carboxylic acid (1.252 g) as yellow crystals.

Workup

  1. stirringAfter stirring for hour at room temperature
  2. stirringAfter stirring for 2 hours at room temperature
  3. washwashed with water
  4. dry with materialAfter drying over magnesium sulfate
  5. extractionthe chloroform extract
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. washThe precipitate was washed with a cold chloroform

Sources & evidence

ORD record
ord-79d8841f82eb4e608da942560e599f62
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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