Water → HCID 54457780, compound

HRID 848745Notes

Reaction equation

HRID 848745 reaction equation
[C:1]([C:4]1[C:13]([NH:14][C:15]([C:17](N)=[O:18])=O)=[CH:12][C:11]([O:20][CH3:21])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)(=[O:3])[CH3:2].[OH2:22].[CH3:23]N(C)C=O>>[CH3:23][O:22][C:17]([C:15]1[NH:14][C:13]2[C:4](=[C:5]3[C:10](=[C:11]([O:20][CH3:21])[CH:12]=2)[N:9]=[CH:8][CH:7]=[CH:6]3)[C:1](=[O:3])[CH:2]=1)=[O:18]

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 20564283HCID 20564283, compound

Product 1

HCID 54457780HCID 54457780, compound

Procedure

2 g of anhydrous potassium tert.-butylate are added to a solution of 2.5 g of N-(5-acetyl-8-methoxyquinolin-6-yl)oxamide acid methyl ester in 50 ml of anhydrous N,N-dimethylformamide and the whole is heated, with the exclusion of water, for 10 hours at 130°. The solution is then allowed to cool and is evaporated to dryness in vacuo. The residue is treated in succession with 2 N acetic acid and water. By chromatographic purification on silica gel and fractionated crystallisation from N,N-dimethylformamide, the 6-methyoxy-1-oxo-1,4-dihydro-4,7-phenanthroline-3-carboxylic acid methyl ester having a melting point of 280° (with decomposition) is obtained.

Workup

  1. temperatureto cool
  2. customis evaporated to dryness in vacuo
  3. additionThe residue is treated in succession with 2 N acetic acid and water
  4. customBy chromatographic purification on silica gel
  5. customcrystallisation from N,N-dimethylformamide

Sources & evidence

ORD record
ord-cb1a3fa8e6a9414ea01de96ca216bb5d
Source dataset
uspto-grants-1981_10
Patent number
US04297358

Reaction notes

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