Nitric Acid → HCID 178433429, compound

HRID 508461Notes

Reaction equation

HRID 508461 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:7]([OH:13])=[N:8][C:9]([CH3:12])=[CH:10][CH:11]=1>>[Br:5][C:6]1[C:7]([OH:13])=[N:8][C:9]([CH3:12])=[C:10]([N+:1]([O-:4])=[O:2])[CH:11]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178423588HCID 178423588, compound

Product 1

HCID 178433429HCID 178433429, compound

Procedure

In a 500 ml single-necked round-bottomed flask, 230 ml of a 65% ageous HNO3 solution is added and stirred under cooling (ice/water cooling bath). 7.00 g of 3-bromo-6-methyl-pyridin-2-ol 2 at ambient temperature is introduced portion-wise. Stirring is continued for 3.5 hours at ambient temperature. After pouring the mixture into 200 ml of an ice/water mixture (pH 1), the water phase is extracted with AcOEt. The organic phase is washed twice with water brought to pH 4 by adding ageous NaOH solution (pH meter), then dried over sodium sulfate, filtered and concentrated in vacuo to give 7.52 g of a yellow solid. This crude material is suspended in diethyl ether and stirred for 1 hour at ambient temperature, filtered, washed with the same solvent and dried to give 3.89 g of the compound as a yellow-orange solid (m.p. >220° C.).

Workup

  1. stirringStirring
  2. extractionthe water phase is extracted with AcOEt
  3. washThe organic phase is washed twice with water
  4. additionby adding ageous NaOH solution (pH meter)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7f5a5985c9944e88e8068f7a9b512b7
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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