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

HRID 1696527Notes

Reaction equation

HRID 1696527 reaction equation
[CH2:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:3](=[O:4])[CH2:2]1.O.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[N+:13]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:3](=[O:4])[CH2:2][CH2:1]2)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 64796Hydrocarbostyril

Product 1

HCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of hydrocarbostyril (7.8 g, 0.53 mol) in conc. H2SO4 (200 mL) was slowly added H2O (50 mL) at −10° C. Conc. HNO3 (70%, 4.0 mL) was added dropwise at −10° C. The yellow solution was stirred at −10° C. for 10 min and then carefully quenched with ice H2O (500 mL). The precipitated yellow solid was filtered, washed with H2O and dried under vacuum to obtain 6-nitro-3,4-dihydroquinolin-2(1H)-one (7.9 g, 78% yield). 1H NMR (400 Mhz, CDCl3): δ 9.28 (s, 1H), 8.12 (m, 2H), 6.95 (d, J=9.2 Hz, 1H), 3.12 (t, J=7.2 Hz, 2H), 2.75 (d, J=7.2 Hz, 2H).

Workup

  1. customat −10° C
  2. customcarefully quenched with ice H2O (500 mL)
  3. filtrationThe precipitated yellow solid was filtered
  4. washwashed with H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-bdb481a42723404e8707c5305fd69052
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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