Nitric Acid → 6-Amino-5-nitronicotinic acid

HRID 1644585Notes

Reaction equation

HRID 1644585 reaction equation
[N+:1]([O-:4])(O)=[O:2].[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=1>S(=O)(=O)(O)O>[NH2:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 184966-Aminonicotinic acid

Product 1

HCID 2718816-Amino-5-nitronicotinic acidYield 36%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of concentrated sulfuric acid (7.5 ml) and concentrated nitric acid (7.5 ml) was added dropwise to a solution of 6-aminonicotinic acid (15 g) in concentrated sulfuric acid (30 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 3 hrs and poured into ice water, and the mixture was stirred for 30 min. The precipitated crystals were collected by filtration and washed with water. The obtained crystals were suspended in concentrated sulfuric acid (60 ml), and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was adjusted with sodium hydroxide to pH 4, and the precipitated crystals were collected by filtration to give the title compound (7.26 g, yield 36%) as pale-as yellow crystals. purity 94%. M+H: 184.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 min
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. stirringthe mixture was stirred at 100° C. for 2 hr
  6. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-8444deed2ad64593bdab75574cf2c95c
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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