Nitric Acid → 6-Chloro-4-hydroxy-3-nitro-chromen-2-One

HRID 897245Notes

Reaction equation

HRID 897245 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11](=[O:16])[CH:10]=[C:9]2[OH:17]>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11](=[O:16])[C:10]([N+:1]([O-:4])=[O:2])=[C:9]2[OH:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546863486-Chloro-4-hydroxycoumarin

Product 1

HCID 546845326-Chloro-4-hydroxy-3-nitro-chromen-2-One

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Red fuming nitric acid (10 mL) was added to a stirred suspension of 6-Chloro-4-hydroxy-chromen-2-one (2.0 g, 10.17 mmol) in chloroform (200 mL) at 0° C. The resultant solution was stirred at 0° C. for 1.5 h, quenched with water (80 mL), the organics separated and treated with saturated NaHCO3 when a thick yellow solid fell out of solution. The solid was filtered and the filtrate acidified with 3N HCl (pH 2) and extracted with chloroform. The organic extracts were dried to a yellow powder and all solids were combined and identified as 6-chloro-4-hydroxy-3-nitro-chromen-2-one. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.78 (d, 1H), 7.55 (dd, 1H), 7.23 (d, 1H).

Workup

  1. customquenched with water (80 mL)
  2. customthe organics separated
  3. additiontreated with saturated NaHCO3 when a thick yellow solid
  4. filtrationThe solid was filtered
  5. extractionextracted with chloroform
  6. customThe organic extracts were dried to a yellow powder

Sources & evidence

ORD record
ord-872db64a62e942ee94865456d14c28b4
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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