Water → HCID 21533367, compound

HRID 1657455Notes

Reaction equation

HRID 1657455 reaction equation
C(O[C:4](=O)[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.O.P(Cl)(Cl)([Cl:30])=O>>[C:6]([C:5]1[CH:11]=[N:12][C:13]2[C:18]([C:4]=1[Cl:30])=[CH:17][C:16]([CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)=[CH:15][CH:14]=2)([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 68135695HCID 68135695, compound

Product 1

HCID 21533367HCID 21533367, compound

Procedure

10 g of p-cycloheptyl-anilinomethylene-malonic acid diethyl ester are dissolved in 50 ml of phosphorus oxychloride, 0.2 g of polyphosphoric acid is added and the mixture is boiled for 2 hours under reflux, with exclusion of water. The mixture is then evaporated to dryness in vacuo, the evaporation residue is partitioned between 3 times 100 ml of methylene chloride and 3 times 100 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 a little silica gel and crystallised from petroleum ether to give 3-carboethoxy-4-chloro-6-cycloheptyl-quinoline of melting point 61°-62°C.

Workup

  1. customThe mixture is then evaporated to dryness in vacuo
  2. customthe evaporation residue is partitioned between 3 times 100 ml of methylene chloride and 3 times 100 ml of 2 N sodium hydroxide solution
  3. washthe organic solution is washed until neutral,
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness in vacuo
  6. additionThe evaporation residue is treated with active charcoal
  7. customa little silica gel and crystallised from petroleum ether

Sources & evidence

ORD record
ord-171a2b57d52d4d6ca1f946f30029151c
Source dataset
uspto-grants-1976_06
Patent number
US03960868

Reaction notes

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