Nitric Acid → HCID 178526876, compound

HRID 639614Notes

Reaction equation

HRID 639614 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[CH:5]=2)[CH2:3][CH2:2]1.[N+:12]([O-])([OH:14])=[O:13]>CC(O)=O.CCOC(C)=O>[CH:1]1([C:4]2[N:9]=[C:8]([OH:10])[C:7]([N+:12]([O-:14])=[O:13])=[C:6]([OH:11])[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 178516635HCID 178516635, compound

Product 1

HCID 178526876HCID 178526876, compoundYield 514%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Conditions

Temperature
30 °C

Procedure

6-Cyclopropyl-2,4-dihydroxy-pyridine (1 g, 6.6 mmol) was suspended in AcOH:EtOAc (4:1, 10 mL) at room temperature. The mixture was warmed to 30° C. and a small portion of fuming nitric acid (0.05 ml, 1.2 mmol) was added dropwise, keeping the temperature between 30 and 35° C. Upon addition the mixture became a clear solution. The remainder of the fuming nitric acid (0.25 ml, 6.3 mmol) was added dropwise. The clear solution was allowed to cool to room temperature upon which a precipitate started to form. The mixture was stirred at room temperature overnight. The solid was collected by filtration, washed with cold water and Et2O and dried in vacuo at room temperature over the weekend to give the title compound (1.21 g) as a yellow powder.

Workup

  1. customthe temperature between 30 and 35° C
  2. additionUpon addition the mixture
  3. temperatureto cool to room temperature upon which a precipitate
  4. customto form
  5. filtrationThe solid was collected by filtration
  6. washwashed with cold water and Et2O
  7. customdried in vacuo at room temperature over the weekend

Sources & evidence

ORD record
ord-699ba7392eb04e3ab88e5aceacec5a4a
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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