Acetic Acid → HCID 13288068, compound

HRID 1903903Notes

Reaction equation

HRID 1903903 reaction equation
[OH-].[Na+].[NH2:3][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]([O:20]CC)=[O:19])=[CH:5]1.C(O)(=O)C>O>[NH2:3][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

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 10516574HCID 10516574, compound

Product 1

HCID 13288068HCID 13288068, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4.4 g (0.11 mole) of sodium hydroxide in 350 ml of water was added 3.0 g (0.047 mole) of ethyl 5-amino-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylate (Example 1). The resulting slurry was stirred at about 90° C. for three hours, then cooled to room temperature and neutralized with 9.3 ml of acetic acid. The solid product was collected by filtration and recrystallized from dimethylformamide to give 10.3 g of 5-amino-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid, colorless crystals, m.p. 309°-313° C. (decompn.).

Workup

  1. filtrationThe solid product was collected by filtration
  2. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-fdf97b4f7f584ffc9333f8d57a405d33
Source dataset
uspto-grants-1984_03
Patent number
US04439436

Reaction notes

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