Sulfuric Acid → HCID 23262449, compound

HRID 2306249Notes

Reaction equation

HRID 2306249 reaction equation
N[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2.[OH:15]S(O)(=O)=O.N([O-])=O.[Na+]>O>[OH:15][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 18433605HCID 18433605, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23262449HCID 23262449, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

3-Amino-5-nitroquinoline, as described above in Step C, (4.48 g, 23.68 mmol) was dissolved in H2SO4 (6N aqueous solution, 50 mL, 300 mmol) and cooled to approximately 5° C. A 0° C. solution of NaNO2 (1.63g, 23.68 mmol) in water (5 mL) was added dropwise to the amine solution. After 45 min at 5 to 10° C., the reaction was poured into refluxing 5% aqueous H2SO4 (300 mL). The resulting mixture was heated for 5 min, then cooled and extracted once with CH2Cl2. The aqueous layer was basified with solid NaHCO3 and extracted once with CH2Cl2. The aqueous layer was then neutralized with aqueous HCl and filtered. The filtered solid was dried in vacuo to yield the above-titled compound.

Workup

  1. additionthe reaction was poured
  2. temperatureThe resulting mixture was heated for 5 min
  3. temperaturecooled
  4. extractionextracted once with CH2Cl2
  5. extractionextracted once with CH2Cl2
  6. filtrationfiltered
  7. customThe filtered solid was dried in vacuo

Sources & evidence

ORD record
ord-202f03c399784f9eb896ed2eed642dbd
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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