Nitric Acid → HCID 178524577, compound

HRID 1655599Notes

Reaction equation

HRID 1655599 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[OH:1][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178418543HCID 178418543, compound

Product 1

HCID 178524577HCID 178524577, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Hydroxynicotinic acid was added portionwise to sulfuric acid (50 mL) at 0° C. After complete dissolution, nitric acid (3 mL) was added dropwise to the cooled solution. After the addition was complete, the bath was removed and the solution stirred overnight at ambient temperature. The solution was then heated at 50°-70° C. for one and a half hours. The solution was cooled to ambient temperature and poured onto ice (100 g). The pale yellow solid which resulted was collected by filtration and dried in vacuo at 50° C. to give 7.3 g (87% yield) of the title compound which was used without further purification. 1H NMR (DMSO-d6, 300 MHz) δ 8.51 (d, 1H,J=3), 9.01 (d,2H,J=3).

Workup

  1. additionwas added dropwise to the cooled solution
  2. additionAfter the addition
  3. customthe bath was removed
  4. temperatureThe solution was then heated at 50°-70° C. for one and a half hours
  5. temperatureThe solution was cooled to ambient temperature
  6. additionpoured onto ice (100 g)
  7. customThe pale yellow solid which resulted
  8. filtrationwas collected by filtration
  9. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-331f6fd2b85a4d1fb0c4e68a6129cf44
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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