Phosphorus oxychloride → HCID 14500574, compound

HRID 1761522Notes

Reaction equation

HRID 1761522 reaction equation
O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:3]=12.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:3]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469464HCID 178469464, compound

Product 1

HCID 14500574HCID 14500574, compound

Procedure

A solution of 5 g of ethyl 5,6,7,8,9,10-hexahydro-4-hydroxycycloocta[b]pyridine-3-carboxylate in 20 ml of phosphorus oxychloride is refluxed for one hour and evaporated to dryness under reduced pressure. A solution of the residue in methylene chloride is treated with ice and water, and basified with 10 N sodium hydroxide. The layers are separated, the aqueous phase reextracted with methylene chloride, and the combined organic layers dried with magnesium sulfate, filtered, and solvent removed at reduced pressure to obtain ethyl 5,6,7,8,9,10-hexahydro-4-chlorocycloocta[b]pyridine-3-carboxylate as an oil which solidifies on standing, m.p. 33°-36°.

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionA solution of the residue in methylene chloride is treated with ice and water
  3. customThe layers are separated
  4. dry with materialthe combined organic layers dried with magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed at reduced pressure

Sources & evidence

ORD record
ord-50eafbbff8624ae5834e719926f45e2a
Source dataset
uspto-grants-1989_05
Patent number
US04826854

Reaction notes

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