Water → HCID 21533367, compound

HRID 1657453Notes

Reaction equation

HRID 1657453 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[CH:13][C:12]([CH:17]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:11][CH:10]=2)([O:3][CH2:4][CH3:5])=[O:2].O.P(Cl)(Cl)([Cl:27])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:27])=[CH:13][C:12]([CH:17]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:11][CH:10]=2)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178469507HCID 178469507, compound

Product 1

HCID 21533367HCID 21533367, compound

Procedure

A solution of 100 g of 3-carboethoxy-4-hydroxy-6-cycloheptyl-quinoline in 670 ml of phosphorus oxychloride is boiled for 21/2 hours under reflux, with exclusion of water. It is then evaporated to dryness in vacuo, the residue is partitioned between 3 times 500 ml of methylene chloride and 3 times 500 ml of 2 N sodium hydroxide solution and the organic solution is washed until neutral, dried over sodium sulphate and evaporated to dryness in vacuo. The evaporation residue is treated with active charcoal and then recrystallised twice from petroleum ether. 3-Carboethoxy-4-chloro-6-cycloheptyl-quinoline of melting point 61°-62°C is thus obtained.

Workup

  1. custom2 hours
  2. customIt is then evaporated to dryness in vacuo
  3. customthe residue is partitioned between 3 times 500 ml of methylene chloride and 3 times 500 ml of 2 N sodium hydroxide solution
  4. washthe organic solution is washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness in vacuo
  7. additionThe evaporation residue is treated with active charcoal
  8. customrecrystallised twice from petroleum ether

Sources & evidence

ORD record
ord-6c47a342c99647cab270b3f0ab8bdb2a
Source dataset
uspto-grants-1976_06
Patent number
US03960868

Reaction notes

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