Nitric Acid → 4-Hydroxy-3-nitro-2(1H)-quinolinone

HRID 462057Notes

Reaction equation

HRID 462057 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546808712(1H)-Quinolinone, 4-hydroxy-

Product 1

HCID 546801624-Hydroxy-3-nitro-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 4-hydroxycarbostyril (1.5g; 0.0093 mole) in glacial acetic acid (10 ml) was well stirred during the addition of concentrated nitric acid (2.5 ml d, 1.42) and the mixture shaken at 95° C for a few minutes until dissolution was complete. The deep red solution soon deposited yellow crystals which after cooling were filtered off and washed with acetic acid and then ethanol. Drying in vacuo over phosphorus pentoxide afforded analytically pure 3-nitro compound m.p. 216° C (decomp) (Found C, 52.74; H, 3.14; N, 13.57; C9H6N2O4 required; C, 52.44; H, 2.93; N, 13.59%).

Workup

  1. temperatureThe deep red solution soon deposited yellow crystals which after cooling
  2. filtrationwere filtered off
  3. washwashed with acetic acid
  4. dry with materialDrying in vacuo over phosphorus pentoxide
  5. customafforded analytically pure 3-nitro compound m.p. 216° C (decomp) (Found C, 52.74; H, 3.14; N, 13.57; C9H6N2O4 required; C, 52.44; H, 2.93; N, 13.59%)

Sources & evidence

ORD record
ord-29fccf17ee524a9093947d63a39ec47c
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Reaction notes

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