Nitric Acid → HCID 18983607, compound

HRID 1440429Notes

Reaction equation

HRID 1440429 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH3:15])([CH3:14])[CH2:6][C:5]1=[O:16])([CH3:3])[CH3:2].OS(O)(=O)=O.[N+:22]([O-])([OH:24])=[O:23]>>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N+:22]([O-:24])=[O:23])=[CH:11][CH:12]=2)[C:7]([CH3:14])([CH3:15])[CH2:6][C:5]1=[O:16])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 15338266HCID 15338266, compound2×

Product 1

HCID 18983607HCID 18983607, compound

Conditions

Temperature
-5 °C

Procedure

N-Isopropyl 4,4,-dimethyl-2-oxo-quinoline (Compound 39, 472 mg, 2.18 mmol) was added dropwise to H2SO4 (con. 0.3 mL) cooled to -5° C. with a salt-ice bath. To this brown oil was added a mixture of HNO3 (0.16 mL) and H2SO4 (0.65 mL) at a rate so slow that the internal temperature did not exceed 0° C. The resulting dark oil was stirred vigorously for 10 minutes, followed by addition of ice-water. The yellow reaction mixture was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with NaHCO3 (10%), dried over MgSO4 and concentrated to give yellow solids. 1H NMR d 1.34 (s, 6H), 1.53(d, J=6.8 Hz, 6H), 2.48 (s, 2H), 4.70-4.79 (m, 1H), 7.25 (d, J=6.3 Hz, 1H), 8.10-8.15 (m, 2H).

Workup

  1. additionTo this brown oil was added
  2. customdid not exceed 0° C
  3. extractionThe yellow reaction mixture was extracted with ethyl acetate (2×5 mL)
  4. washThe combined organic layers were washed with NaHCO3 (10%)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give yellow solids

Sources & evidence

ORD record
ord-6aa9c5d0f6534bbb8419055bec62c5ce
Source dataset
uspto-grants-1996_03
Patent number
US05498755

Reaction notes

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