Phosphorus oxychloride → HCID 18548986, compound

HRID 276877Notes

Reaction equation

HRID 276877 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178504176HCID 178504176, compound

Product 1

HCID 18548986HCID 18548986, compound

Procedure

To 500 mg of 4-hydroxy-6-trimethylsilanylethynyl-[1.7]naphthyridine-3-carbonitrile under an inert atmosphere was added 10 mL of phosphorous oxychloride. After two hours at reflux, the excess phosphorous oxychloride was removed in vacuo and ice-water, chloroform, a tract of methanol, and aqueous saturated sodium bicarbonate were added. The chloroform layer was washed with brine, dried with sodium sulfate, and evaporated to give 626 mg of crude 4-chloro-6-trimethylsilanylethynyl-[1.7]naphthyridine-3-carbonitrile as a yellowish solid, which was used in the following step.

Workup

  1. temperatureAfter two hours at reflux
  2. customthe excess phosphorous oxychloride was removed in vacuo and ice-water, chloroform
  3. additiona tract of methanol, and aqueous saturated sodium bicarbonate were added
  4. washThe chloroform layer was washed with brine
  5. dry with materialdried with sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-4e564ad6fbf143038b847a336dd2cf8f
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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