Water → HCID 53859167, compound

HRID 848747Notes

Reaction equation

HRID 848747 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11](Cl)[C:12]2[C:21]([N:22]=1)=[CH:20][C:19]([O:23][CH3:24])=[C:18]1[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]1)=[O:8].O>CN(C)C=O>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([O:3][CH2:2][CH3:1])[C:12]2[C:21]([N:22]=1)=[CH:20][C:19]([O:23][CH3:24])=[C:18]1[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]1)=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 54343969HCID 54343969, compound

Product 1

HCID 53859167HCID 53859167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of sodium ethylate are added to a solution of 6.2 g of 1-chloro-6-methoxy-4,7-phenanthroline-3-carboxylic acid methyl ester in 100 ml of anhydrous N,N-dimethylformamide and the mixture is heated, whilst stirring and with the exclusion of water, for 10 hours at 100°. The solution is then evaporated to dryness in vacuo, the residue is divided between three times 200 ml of chloroform and 200 ml of water, the organic phases are dried over sodium sulphate and evaporated to dryness in vacuo. By fractionated crystallisation from ethanol, the 1-ethoxy-6-methoxy-4,7-phenanthroline-3-carboxylic acid methyl ester having a melting point of 188°-190° is obtained from the residue.

Workup

  1. temperaturethe mixture is heated
  2. customThe solution is then evaporated to dryness in vacuo
  3. dry with materialthe organic phases are dried over sodium sulphate
  4. customevaporated to dryness in vacuo
  5. customBy fractionated crystallisation from ethanol

Sources & evidence

ORD record
ord-5c732b273c0a473d81ce809a3720d4da
Source dataset
uspto-grants-1981_10
Patent number
US04297358

Reaction notes

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