Nitric Acid → 4-Hydroxy-3-nitro-5,6,7,8-tetrahydroquinolin-2(1H)-one

HRID 437359Notes

Reaction equation

HRID 437359 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[NH:5][C:4](=[O:12])[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14].O>C(O)(=O)C>[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[NH:5][C:4](=[O:12])[C:3]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 546973614-Hydroxy-5,6,7,8-tetrahydroquinolin-2(1H)-one

Product 1

HCID 546845154-Hydroxy-3-nitro-5,6,7,8-tetrahydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-hydroxy-5,6,7,8-tetrahydrocarbostyril (1.70g; 0.0103 mole) and concentrated nitric acid (2.5 ml; d 1.42), in glacial acetic acid (10 ml) was heated at 100° C till the oxides of nitrogen were evolved and rapidly cooled in ice. Water (40 ml) was added to the red solution to precipitate the yellow-orance 3-nitro derivative. After filtration, thorough washing with water and recrystallisation from acetic acid - ethanol the product had m.p. 241° (d).

Workup

  1. temperaturerapidly cooled in ice
  2. customto precipitate the yellow-orance 3-nitro derivative
  3. filtrationAfter filtration
  4. washthorough washing with water and recrystallisation from acetic acid - ethanol the product

Sources & evidence

ORD record
ord-5684e01494ae42bbaba6a053dfeb86ec
Source dataset
uspto-grants-1977_06
Patent number
US04031099

Reaction notes

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