Nitric Acid → 4-Hydroxy-1-methyl-3-nitro-1,2-dihydroquinolin-2-one

HRID 462065Notes

Reaction equation

HRID 462065 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546864364-Hydroxy-N-methylcarbostyril

Product 1

HCID 546821234-Hydroxy-1-methyl-3-nitro-1,2-dihydroquinolin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 4-hydroxy-1-methyl carbostyril (1.63g; 0.009 mole) in glacial acetic acid (10 ml) was stirred during the addition of concentrated nitric acid (2.5 ml; d, 1.42) and the mixture heated for a few minutes on a steam bath. On cooling the clear red solution deposited yellow crystals of the title compound which were diluted with ethanol, filtered, and washed well with ethanol, m.p. 159°-161° C (Found: C, 54.20; H 3.71; N, 12.42; C10H8N2O4 requires; C, 54.55 H, 3.66; N, 12.72%).

Workup

  1. temperaturethe mixture heated for a few minutes on a steam bath
  2. temperatureOn cooling the clear red solution

Sources & evidence

ORD record
ord-bf0177aefe3a40abadb7cd605ad96c00
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Reaction notes

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