Nitric Acid → HCID 57498010, compound

HRID 1454935Notes

Reaction equation

HRID 1454935 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8][CH:7]=1>OS(O)(=O)=O.O>[Br:5][C:6]1[C:15]2[C:10](=[C:11]([N+:1]([O-:4])=[O:2])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8][CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 737434-Bromoisoquinoline

Product 1

HCID 57498010HCID 57498010, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Under argon, at room temperature, 65% HNO3 (200 mmol, 13.85 ml) is added in small portions to a solution of 4-bromoisoquinoline (100 mmol, 21.24 g) in 36N H2SO4 (50 ml). The reaction mixture is stirred for 3 h at room temperature. It is cooled to 0° C. and is then diluted with water. A yellow precipitate forms. It is filtered. The pH of the filtrate is adjusted to pH 10 by slow addition of 5N NaOH. The white precipitate which appears is extracted with CH2Cl2. This organic solution is washed with brine, dried over Na2SO4 and then evaporated under vacuum. The residue is purified by eluting on silica gel with an AcOEt/petroleum ether mixture. The purified product is recrystallized from absolute ethanol (EtOH).

Workup

  1. temperatureIt is cooled to 0° C.
  2. filtrationIt is filtered
  3. additionThe pH of the filtrate is adjusted to pH 10 by slow addition of 5N NaOH
  4. extractionThe white precipitate which appears is extracted with CH2Cl2
  5. washThis organic solution is washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated under vacuum
  8. customThe residue is purified
  9. washby eluting on silica gel with an AcOEt/petroleum ether mixture
  10. customThe purified product is recrystallized from absolute ethanol (EtOH)

Sources & evidence

ORD record
ord-1217b01496324d11a2919ffa4c8c4aa6
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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