Sulfuric Acid → HCID 86732834, compound

HRID 525969Notes

Reaction equation

HRID 525969 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=3)[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[N+:27]([O-])([O-:29])=[O:28].[K+]>>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:27]([O-:29])=[O:28])[C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=3)[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 82250420HCID 82250420, compound

Product 1

HCID 86732834HCID 86732834, compoundYield 60.6%

Conditions

Temperature
0 °C

Procedure

1-Cyclopropyl-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (Example 50b) (20 g, 69.1 mmol) was dissolved in sulfuric acid (44.2 ml, 830 mmol) with stirring. The thick dark solution was cooled to 0° C. and potassium nitrate (10.48 g, 104 mmol) was added in small portions, while the temperature was maintained below 10° C. by use of an ice-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 overnight. LCMS showed completion of reaction. The mixture was poured into ice-water (300 mL). A yellow solid precipitated out and was collected by filtration, washed with water and ethanol, and dried in vacuo to afford 1-cyclopropyl-6,7-dimethoxy-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (14 g, 41.9 mmol, 60.6% yield) as a pale yellow solid. LCMS: [M+H]+: 335.1.

Workup

  1. temperaturewas maintained below 10° C. by use of an ice-water bath
  2. additionAfter the addition
  3. temperatureto warm up to r.t.
  4. stirringstirred overnight
  5. customcompletion of reaction
  6. customA yellow solid precipitated out and
  7. filtrationwas collected by filtration
  8. washwashed with water and ethanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-29213fe4e8bc48c19b60ffefd2becfd6
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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