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

HRID 1292484Notes

Reaction equation

HRID 1292484 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8](=[O:16])[CH:7]=1.O>C(O)(=O)C>[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8](=[O:16])[C:7]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 546808712(1H)-Quinolinone, 4-hydroxy-

Product 1

HCID 546801624-Hydroxy-3-nitro-2(1H)-quinolinoneYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Fuming nitric acid (262 mL) was added at about 20° C. to a suspension of 4-hydroxy-2(1H)-quinolinone (1.0 Kg) in acetic acid (7.57 L). The mixture was heated at 40° C. for 2.5 h. The resulting solution was cooled to about 20° C. and poured into 8 L of water. The resulting solution was stirred for 20 min, filtered, washed with water until the filtrate was neutral, and dried. The product 4-hydroxy-3-nitro-2(1H)-quinolinone was isolated in 98% yield and showed only one spot upon analysis by thin layer chromatography (silica gel, 20:80 (V/V) chloroform in methanol).

Workup

  1. temperatureThe resulting solution was cooled to about 20° C.
  2. filtrationfiltered
  3. washwashed with water until the filtrate
  4. customdried

Sources & evidence

ORD record
ord-dc11c52aea894a2dac5abc9fb45b7e17
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

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