Nitric Acid → 6-Nitro-3,4-dihydroquinolin-2(1H)-one

HRID 723890Notes

Reaction equation

HRID 723890 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].O.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][C:2](=[O:11])[CH2:3][CH2:4]2)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962Water2×HCID 64796Hydrocarbostyril

Product 1

HCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3,4-Dihydro-2(1H)-quinolinone (1.0 g, 6.70 mmol) is dissolved in 20 mL of concentrated sulfuric acid at −10° C., and then 5 mL of water is added slowly to the solution. After 5 minutes, 61% nitric acid (0.5 mL, 6.70 mmol) is added dropwise to the solution. The reaction mixture turns from yellow to dark red, and eventually solidifies. After 1 hour, water (50 mL) is added slowly at −10° C. and precipitate appears. The solution is poured into a separatory funnel, extracted with ethyl acetate (20 mL×2) and washed with saline (20 mL). The organic layers are collected and dried over MgSO4. Solvent is removed and the title compound is obtained as a pale yellow solid (1.0 g, 76%); 1H NMR (300 MHz, DMSO) δ 10.66 (s, 1H), 8.08–8.01 (m, 2H), 6.96 (d, 1H), 2.98 (t, 2H), 2.49 (dd, 2H).

Workup

  1. waitAfter 1 hour
  2. additionThe solution is poured into a separatory funnel
  3. extractionextracted with ethyl acetate (20 mL×2)
  4. washwashed with saline (20 mL)
  5. customThe organic layers are collected
  6. dry with materialdried over MgSO4
  7. customSolvent is removed

Sources & evidence

ORD record
ord-06bce340b43e480792699d113cbe0b78
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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