Nitric Acid → HCID 54705784, compound

HRID 1658090Notes

Reaction equation

HRID 1658090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([N+:14]([O-:16])=[O:15])=[C:5]2[OH:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 547057622,4-QUINOLINEDIOL

Product 1

HCID 54705784HCID 54705784, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 6-chloro-4-hydroxycarbostyril (1.82g; 0.0093 mole) in glacial acetic acid (10 ml) was shaken with concentrated nitric acid (2.5 ml; d, 1.42) and the mixture heated on a water bath at 100°C until a clear solution resulted. Cooling of the orange solution gave a bright yellow solid which was filtered, washed well with acetic acid and then ethanol. Drying in vacuo over P2O5NaOH gave analytically pure 6-chloro-4-hydroxy-3-nitrocarbostyril: decomposes 200°C. (Found: C, 45.31; H, 2.31 N, 11.93; Cl, 14.78; C9H5N2CIO4 requires; C, 44.93; H, 2.09; N, 11.64 Cl, 14.74%).

Workup

  1. customresulted
  2. temperatureCooling of the orange solution
  3. customgave a bright yellow solid which
  4. filtrationwas filtered
  5. washwashed well with acetic acid
  6. customDrying in vacuo over P2O5NaOH

Sources & evidence

ORD record
ord-c5b78ea78444428c8aae569e89ac3e75
Source dataset
uspto-grants-1976_06
Patent number
US03962445

Reaction notes

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