Sulfuric Acid → HCID 12478765, compound

HRID 525896Notes

Reaction equation

HRID 525896 reaction equation
[CH2:1]([N:3]1[C:12]2[CH:11]=[C:10]3[O:13][CH2:14][O:15][C:9]3=[CH:8][C:7]=2[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].OS(O)(=O)=O.[N+:25]([O-])([O-:27])=[O:26].[K+]>O>[CH2:1]([N:3]1[C:12]2[CH:11]=[C:10]3[O:13][CH2:14][O:15][C:9]3=[C:8]([N+:25]([O-:27])=[O:26])[C:7]=2[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4628Oxolinic acidHCID 24434Potassium Nitrate

Product 1

HCID 12478765HCID 12478765, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5-Ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (50 g, 191 mmol) was dissolved in H2SO4 (112 ml, 2105 mmol) with stirring. The thick solution was cooled to 0° C. and potassium nitrate (21.29 g, 211 mmol) was added in small portions. The temperature of the reaction mixture was maintained below 10° C. by use of an iced water bath. After the addition, the mixture was kept under 10° C. for 1 h, and then was allowed to warm up to r.t. and stirred for overnight. It was poured into iced water (2 L). The yellow precipitates were collected by filtration, washed with water and ethanol, and dried in vacuo to afford 5-ethyl-9-nitro-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (61 g, 187 mmol, 98% yield) as a light brown solid. LCMS: (M+H)+: 307.4.

Workup

  1. temperatureThe temperature of the reaction mixture was maintained below 10° C. by use of an iced water bath
  2. additionAfter the addition
  3. temperatureto warm up to r.t.
  4. stirringstirred for overnight
  5. customThe yellow precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water and ethanol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-31c85623df9147a09e6b95b11f28d873
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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