Potassium Carbonate → HCID 10516574, compound

HRID 1903902Notes

Reaction equation

HRID 1903902 reaction equation
[OH:1][C:2]1[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][O:14][C:8]3=[CH:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].[N+:26](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O>[NH2:26][N:5]1[C:6]2[CH:7]=[C:8]3[O:14][CH2:13][O:12][C:9]3=[CH:10][C:11]=2[C:2](=[O:1])[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842571,3-Dioxolo[4,5-g]quinoline-7-carboxylic acid, 8-hydroxy-, ethyl esterHCID 87140O-(2,4-dinitrophenyl)hydroxylamine2×

Product 1

HCID 10516574HCID 10516574, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 12.8 g (0.049 mole) of ethyl 8-hydroxy-1,3-dioxolo[4,5-g]quinoline-7-carboxylate and 13.5 g (0.098 mole) of potassium carbonate in 500 ml of dimethylformamide was added 11.7 g (0.059 mole) of O-(2,4-dinitrophenyl)hydroxylamine. The reaction mixture was stirred overnight at room temperature. An additional 5.0 g of O-(2,4-dinitrophenyl)hydroxylamine and 300 ml of dimethylformamide were then added and stirring was continued again overnight. The solvent was removed in vacuo, the residue stirred in 500 ml of water, and the product was collected by filtration and recrystallized from dimethylformamide to give 7.6 g of ethyl 5-amino-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylate, pale orange crystals, m.p. 251°-253° C.

Workup

  1. stirringstirring
  2. waitwas continued again overnight
  3. customThe solvent was removed in vacuo
  4. stirringthe residue stirred in 500 ml of water
  5. filtrationthe product was collected by filtration
  6. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-9774fd5c9e3040cfa9d8652c2db256e3
Source dataset
uspto-grants-1984_03
Patent number
US04439436

Reaction notes

Loading…