Nitric Acid → HCID 86706568, compound

HRID 2174557Notes

Reaction equation

HRID 2174557 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:13])=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[I:14].[N+:15]([O-])([OH:17])=[O:16]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:13])=[C:7]([N+:15]([O-:17])=[O:16])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[I:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 68290699HCID 68290699, compound2×

Product 1

HCID 86706568HCID 86706568, compoundYield 82%

Procedure

7-Chloro-4-hydroxy-6-iodo-2(1H)-quinolinone (Intermediate 142) (300 mg, 0.933 mmol) was dissolved in nitric acid (1 mL, 22.38 mmol) and the reaction mixture was stirred 15 min at room temperature and heated 30 min at 75° C. After cooling, the reaction mixture was poured into ice water and the precipitate was filtered and dried to give the title compound 7-chloro-4-hydroxy-6-iodo-3-nitro-2(1H)-quinolinone (280 mg, 0.764 mmol, 82% yield) as yellow solid. LCMS: (M+H)+=367; Rt=2.06 min.

Workup

  1. temperatureheated 30 min at 75° C
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-bacfc932342148aeae628ce471b32843
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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