Water → HCID 86738072, compound

HRID 848746Notes

Reaction equation

HRID 848746 reaction equation
C(O[C:4](=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])C.C([C:14]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([O:27][CH3:28])=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[N:19]2)(=O)C.[OH2:29].[C:30]1([CH3:36])C=CC=CC=1>C(O)C.CC[O-].[Na+]>[CH2:8]([O:7][C:5](=[O:6])[C:4](=[O:10])[CH2:36][C:30]([C:23]1([N+:24]([O-:26])=[O:25])[CH:22]=[C:21]([O:27][CH3:28])[C:20]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:14]1)=[O:29])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7268Diethyl OxalateHCID 20564287HCID 20564287, compound

Product 1

HCID 86738072HCID 86738072, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

30 ml of oxalic acid diethyl ester are added to a solution of 10 g of 5-acetyl-6-nitro-8-methoxyquinoline in 200 ml of ethanol and 3 g of sodium ethylate, and refluxed, whilst stirring, for 12 hours with the exclusion of water. 100 ml of toluene are then added and the reaction mixture is heated for a further 5 hours, then evaporated to dryness in vacuo and the residue triturated first with 2 N acetic acid then with water. The crude 4-(6-nitro-8-methoxyquinolin-6-yl)-2,4-dioxobutyric acid ethyl ester obtained in this manner is further processed without further purification.

Workup

  1. temperaturerefluxed
  2. temperaturethe reaction mixture is heated for a further 5 hours
  3. customevaporated to dryness in vacuo
  4. customthe residue triturated first with 2 N acetic acid

Sources & evidence

ORD record
ord-dde8fb10f5494d3ba83a48a23c560712
Source dataset
uspto-grants-1981_10
Patent number
US04297358

Reaction notes

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