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

HRID 1956462Notes

Reaction equation

HRID 1956462 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].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[N+:12]([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-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 64796Hydrocarbostyril

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 3,4-dihydroquinolin-2-(1H)-one (1.50 g) in 78% sulfuric acid (300 mL) at RT, a mixture of 69% nitric acid (0.84 mL) in 78% sulfuric acid (60 mL) was added. The reacting mixture was stirred at RT for 15 min, poured into ice-water, and extracted with methylene chloride (3×200 mL). The organic extracts were combined, washed with brine (4×), dried over anhydrous magnesium sulfate, filtered and concentrated onto silica gel. The residue was loaded onto a column of silica gel, and eluted with 3% methanol in chloroform. Collection and concentration of appropriate fractions provided the nitroquinolinone 11-2.

Workup

  1. additionwas added
  2. extractionextracted with methylene chloride (3×200 mL)
  3. washwashed with brine (4×)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. washeluted with 3% methanol in chloroform
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-ebf8184d999f490fb9c4ef745d28a077
Source dataset
uspto-grants-1998_07
Patent number
US05780480

Reaction notes

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