Nitric Acid → 8-Bromo-5-nitroquinoline

HRID 2110434Notes

Reaction equation

HRID 2110434 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1401098-Bromoquinoline

Product 1

HCID 157091828-Bromo-5-nitroquinolineYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

8-Bromoquinoline (25.00 g, 120.2 mmol) was dissolved in sulfuric acid (82.5 mL) at rt and then cooled to 0° C. HNO3 (fuming, 32.5 mL) was then slowly added over a 10 minute period. The reaction was then warmed to rt and then to 65° C. After 48 h at 65° C., the reaction was cooled to rt and poured onto 500 g of ice. This solution was extracted with methylene chloride (5×200 mL). The organic layers were washed once with brine and dried over anhydrous sodium sulfate. Concentration gave the crude compound 464A as a light yellow solid (28.6 g, 94%). HPLC: 98% at 2.717 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. temperatureThe reaction was then warmed to rt
  2. customto 65° C
  3. temperaturethe reaction was cooled to rt
  4. extractionThis solution was extracted with methylene chloride (5×200 mL)
  5. washThe organic layers were washed once with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-8cdcf29ad35449cdb41ee96fb6eea6b3
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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