Nitric Acid → 1-Ethyl-4-hydroxy-3-nitro-1H-quinolin-2-one

HRID 1658095Notes

Reaction equation

HRID 1658095 reaction equation
[CH2:1]([N:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][C:4]1=[O:5])[CH3:2].[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[CH2:1]([N:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[C:6]([N+:15]([O-:17])=[O:16])[C:4]1=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546846411-Ethyl-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 546838871-Ethyl-4-hydroxy-3-nitro-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1-ethyl-4-hydroxy carbostyril (1.09 g; 0.00575 mole) in glacial acetic acid (5 ml) was swirled during the rapid addition of concentrated nitric acid (1.25 ml; d 1.42) and the dark liquid heated for 5 minutes at 100°C. The yellow solid which separated on cooling was filtered off and washed well with ethanol m.p. 154°-5°C (decomp). (Found;C, 56.54; H, 4.52; N, 11.56; C11H10N2O4 requires; C, 56.41; H, 4.30, N, 11.96%).

Workup

  1. customThe yellow solid which separated
  2. temperatureon cooling
  3. filtrationwas filtered off
  4. washwashed well with ethanol m.p. 154°-5°C (decomp)

Sources & evidence

ORD record
ord-713179d3116d4704abe6957ead6895f3
Source dataset
uspto-grants-1976_06
Patent number
US03962445

Reaction notes

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