Potassium Hydroxide → HCID 13288078, compound

HRID 1903909Notes

Reaction equation

HRID 1903909 reaction equation
[CH2:1]([N:3](C=O)[N:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]1)[CH3:2].[OH-].[K+]>C(O)C.O>[CH2:1]([NH:3][N:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]1)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 13288074HCID 13288074, compound

Product 1

HCID 13288078HCID 13288078, compoundYield 120.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred suspension of 2 g (0.006 mole) of ethyl 5-[ethyl(formyl)amino]-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]-quinoline-7-carboxylate (Example 8) in 53.8 ml of refluxing ethanol was added a solution of 0.9 g (0.014 mole) of potassium hydroxide in 3 ml of water over a period of about two minutes. After a few more minutes of reflux, 30 ml of additional ethanol was added and reflux continued for one hour. The reaction mixture was allowed to stand overnight, then chilled in an ice-bath, and the solid product was collected by filtration and washed with absolute alcohol and ether to give 2 g of 5-(ethylamino)-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid in the form of its potassium salt hemihydrate, m.p. 242° C. (decompn.) after being dried for several days at 75° C. (0.1 mm).

Workup

  1. temperatureAfter a few more minutes of reflux
  2. temperaturereflux
  3. waitto stand overnight
  4. temperaturechilled in an ice-bath
  5. filtrationthe solid product was collected by filtration
  6. washwashed with absolute alcohol and ether

Sources & evidence

ORD record
ord-546a35cfd5f64a4888db35a25144e6c8
Source dataset
uspto-grants-1984_03
Patent number
US04439436

Reaction notes

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