4-Aminobenzoic Acid → 4-Azidobenzoic acid

HRID 1760247Notes

Reaction equation

HRID 1760247 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[N-:15]=[N+:16]=[N-].[Na+]>FC(F)(F)C(O)=O.O>[N:1]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[N+:15]=[N-:16]

Participants

6

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 30341844-Azidobenzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-aminobenzoic acid (2.00 g, 14.00 mmol) in trifluoroacetic acid (10 ml) at 5° C., was added sodium nitrite (3.50 g) portionwise, and the mixture allowed to stir for 30 min. Sodium azide (3.79 g,) was then added portionwise and the mixture stirred for a further 30 min at 0° C. The mixture was diluted with water, and a white solid precipitated. The solid was filtered, washed with cold water and dried, to afford the title compound (1.66 g, 73%).

Workup

  1. stirringthe mixture stirred for a further 30 min at 0° C
  2. customa white solid precipitated
  3. filtrationThe solid was filtered
  4. washwashed with cold water
  5. customdried

Sources & evidence

ORD record
ord-c812eb7fc8f34a30864cb95002a0a733
Source dataset
uspto-grants-2005_01
Patent number
US06841560B2

Reaction notes

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