Nitric Acid → HCID 22605917, compound

HRID 2307271Notes

Reaction equation

HRID 2307271 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N+:3]=1[O-:12].OS(O)(=O)=O.[OH-].[Na+].[N+:20]([O-])([OH:22])=[O:21]>>[Br:1][C:2]1[CH:11]=[C:10]([N+:20]([O-:22])=[O:21])[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N+:3]=1[O-:12]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22605937HCID 22605937, compound

Product 1

HCID 22605917HCID 22605917, compoundYield 83%

Conditions

Temperature
90 °C

Procedure

With efficient ice bath cooling 2-bromo-5,6,7,8-tetrahydro-quinoline 1-oxide (8.0 g, 35 mmol) (S. Zimmermann et al., J. Am. Chem. Soc., 1991, 113, 183) was treated with conc. H2SO4 (65 ml), followed by conc. HNO3 (10 ml). The resulting mixture was heated to 90° C. for 90 min, cooled and poured on crushed ice (200 g). NaOH (28%) was added to reach pH 7 and the aqueous phase extracted with AcOEt. The organic phase was dried (Na2SO4) and concentrated to yield 7.9 g (83%) of the title compound as a yellow oil. MS: m/e=272 (M+).

Workup

  1. temperaturecooled
  2. additionpoured
  3. extractionthe aqueous phase extracted with AcOEt
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c0399fd14af456b831136034904a849
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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