4-Aminobenzoic Acid → 4-Azidobenzoic acid

HRID 928913Notes

Reaction equation

HRID 928913 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[N-:20]=[N+:21]=[N-].[Na+]>O>[N:1]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[N+:20]=[N-:21]

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 30341844-Azidobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

4-aminobenzoic acid (500 mg, 3.65 mmol) was dissolved in 2.5 mL of water and concentrated sulfuric acid (98%, 0.75 mL) and additional water (0.75 mL) were added. The suspension was cooled to 0° C. and a solution of NaNO2 (265 mg, 3.84 mmol) in 0.75 mL of water was added under constant stirring. Sodium azide (293 mg, 4.5 mmol) was added to the brown solution. After additional 15 min of stirring at 0° C. the precipitate was filtered and washed several times with water. The solid was dried to afford 4-azidobenzoic acid (594 mg, 3.64 mmol, 100%) as a white solid. 1H NMR (CD3OD, 500 MHz) δ (ppm): 7.13 (dd, J=1.9, 8.6 Hz, 2H), 8.02 (dd, J=1.9, 8.6 Hz, 2H).

Workup

  1. filtrationwas filtered
  2. washwashed several times with water
  3. customThe solid was dried

Sources & evidence

ORD record
ord-51fe6e5a9b5b40b7a995b44b9246379c
Source dataset
uspto-grants-2016_03
Patent number
US09290791B2

Reaction notes

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