Nitric Acid → HCID 67492909, compound

HRID 1922391Notes

Reaction equation

HRID 1922391 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:18])[CH2:4][CH2:3]1.[N+:19]([O-])([OH:21])=[O:20]>OS(O)(=O)=O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:18])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14969511HCID 14969511, compound

Product 1

HCID 67492909HCID 67492909, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-(1-methylpiperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (305 mg, 1.25 mmol) in conc. H2SO4 (4 mL) was treated with fuming HNO3 (53 μL, 1.25 mmol) at −5 to −10° C. (ice/MeOH) and the resulting solution was stirred for 30 min. at the same temperature. The reaction was quenched with the addition of crushed ice, and then basified with 1 N NaOH, and the product was extracted into CH2Cl2 (2×50 mL). The combined CH2Cl2 layer was dried (Na2SO4), filtered, and the solvent was evaporated. The crude was triturated with hexanes to afford the title compound (320 mg, 88.4%) as a solid. 1H-NMR (CDCl3) δ 8.10-8.05 (m, 2H), 7.33 (d, J=8.7 Hz, 1H), 4.50-4.39 (m, 1H), 3.01-2.90 (m, 4H), 2.67-2.54 (m, 4H), 2.33 (s, 3H), 2.15-2.08 (m, 2H), 1.74-1.70 (m, 2H). MS (ESI): 290.2 (M+1, 100%).

Workup

  1. customThe reaction was quenched with the addition of crushed ice
  2. extractionthe product was extracted into CH2Cl2 (2×50 mL)
  3. dry with materialThe combined CH2Cl2 layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe crude was triturated with hexanes

Sources & evidence

ORD record
ord-667e9def61104ecebf2af24e21c6a156
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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