Oxalyl chloride → 8-chloro-3-[2-(4-morpholinyl)ethyl]-3H-imidazo[4,5-g]quinoline-7-carbonitrile

HRID 2213750Notes

Reaction equation

HRID 2213750 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[C:21]3[C:12](=[CH:13][C:14]4[C:15](=O)[C:16]([C:22]#[N:23])=[CH:17][NH:18][C:19]=4[CH:20]=3)[N:11]=[CH:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:28])=O>CN(C=O)C>[Cl:28][C:15]1[C:14]2[CH:13]=[C:12]3[N:11]=[CH:10][N:9]([CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[C:21]3=[CH:20][C:19]=2[N:18]=[CH:17][C:16]=1[C:22]#[N:23]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 21956471HCID 21956471, compound

Product 1

HCID 219564158-chloro-3-[2-(4-morpholinyl)ethyl]-3H-imidazo[4,5-g]quinoline-7-carbonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A suspension of 190.0 mg (0.59 mmol) of 3-[2-(4-morpholinyl)ethyl]-8-oxo-5,8-dihydro-3H-imidazo[4,5-g]quinoline-7-carbonitrile, 5.45 mL of 2M oxalyl chloride (in methylene chloride) and 5 drops of DMF is heated at reflux temperature for 1.5 hours. After cooling, the solvent is evaporated to dryness. The residue is cooled in an ice bath and neutralized to pH 7 by slow addition of ice-cooled, aqueous saturated sodium bicarbonate solution. The aqueous solution is extracted with methylene chloride. The organic phase is washed with cold brine and dried over sodium sulfate. Removal of the solvent in vacuo gives the crude product. Purification of the crude product by preparative TLC (developing solvent: 5:95 methanol/methylene chloride) gives 122.8 mg (61%) of the product as a yellow solid, mp 205–207° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1.5 hours
  3. temperatureAfter cooling
  4. customthe solvent is evaporated to dryness
  5. temperatureThe residue is cooled in an ice bath
  6. additionneutralized to pH 7 by slow addition of ice-
  7. temperaturecooled
  8. extractionThe aqueous solution is extracted with methylene chloride
  9. washThe organic phase is washed with cold brine
  10. dry with materialdried over sodium sulfate
  11. customRemoval of the solvent in vacuo
  12. customgives the crude product
  13. customPurification of the crude product by preparative TLC (developing solvent: 5:95 methanol/methylene chloride)

Sources & evidence

ORD record
ord-53d8e02a38614263aa14ea9ab05d59c8
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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