Phosphorus oxychloride → HCID 18548986, compound

HRID 1266306Notes

Reaction equation

HRID 1266306 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-bd9111aa02ad4744bf8af8c5bfcb17fb
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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