Nitric Acid → HCID 58504175, compound

HRID 2407740Notes

Reaction equation

HRID 2407740 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 122639922-Amino-6-chloronicotinic acid

Product 1

HCID 58504175HCID 58504175, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Amino-6-chloronicotinic acid (0.479 g) [Helvetica Chimica Acta (1976), 59(1), 222-9] was dissolved in concentrated sulfuric acid (5 mL) and cooled in an ice-saltwater bath and 2.5 mL of fuming nitric acid was then added dropwise with stirring. The ice bath was removed and the reaction mixture was stirred at ambient temperature for 8 hours. The mixture was then added dropwise to a saturated sodium bicarbonate solution (200 mL). The mixture was acidified with 9M aqueous sulfuric acid to pH 2. The solid that formed was filtered and rinsed with water to obtain the title compound (0.340 g) having the following physical data.

Workup

  1. temperaturecooled in an ice-saltwater bath
  2. customThe ice bath was removed
  3. stirringthe reaction mixture was stirred at ambient temperature for 8 hours
  4. additionThe mixture was then added dropwise to a saturated sodium bicarbonate solution (200 mL)
  5. customThe solid that formed
  6. filtrationwas filtered
  7. washrinsed with water

Sources & evidence

ORD record
ord-7cb4d94006d84bfc995daacf8aa0fb02
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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