Phosphorus oxychloride → HCID 18548943, compound

HRID 276838Notes

Reaction equation

HRID 276838 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]#[N:15])=[C:7]2O)[CH3:2].O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH2:1][CH3:2])[N:5]=2)[N:10]=[CH:9][C:8]=1[C:14]#[N:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178466034HCID 178466034, compound

Product 1

HCID 18548943HCID 18548943, compoundYield 100%

Procedure

A solution of 6-ethoxy-4-hydroxyl-[1.5]naphthyridine-3-carbonitrile (500 mg, mmol) in POCl3 was heated at reflux for 2 hrs under nitrogen. The temperature was reduced to 45-50° C. (bath) and heated at this temperature for an additional 2 hrs. After cooling, the solvent was removed by rotary evaporation. The residue was treated with a mixture of ice and water, made basic by using NH4OH, and extracted with CH2Cl2. The combined extracts were washed (brine), dried (Na2SO4), and concentrated to give the title compound as a white solid (522 mg, 100%). H-NMR δ(DMSO-d6): 1.437 (3H, t, CH3), 4.572 (2H, q, CH2), 7.495 (1H, d, C8-H), 8.407 (1H, d, C7-H), 9.108 (1H, s, C2-H).

Workup

  1. temperatureat reflux for 2 hrs under nitrogen
  2. customwas reduced to 45-50° C.
  3. temperatureheated at this temperature for an additional 2 hrs
  4. temperatureAfter cooling
  5. customthe solvent was removed by rotary evaporation
  6. additionThe residue was treated with a mixture of ice and water
  7. extractionextracted with CH2Cl2
  8. washThe combined extracts were washed (brine)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-94adf32a43fc47a0a3181b631c70f7ef
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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