Sodium Azide → 3-Azido-4-methylbenzoic acid

HRID 1374958Notes

Reaction equation

HRID 1374958 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[N-:16]=[N+:17]=[N-].[Na+]>Cl.O>[N:1]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])=[N+:16]=[N-:17]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 755683-Amino-4-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 179730913-Azido-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Amino-4-methyl benzoic acid (2.28 g, 15.1 mmol) was suspended in 65 mL of 2N HCl and chilled to 0° C. A chilled solution of 1.25 g (18.1 mmol) of NaNO2 in 5 mL of water was added slowly, and the solution was stirred for 30 min. The mixture was filtered through a plug of diatomaceous earth, and then returned to a 0° C. bath where 1.08 g (16.6 mmol) of NaN3 dissolved in about 5 mL of water was slowly added. Gas evolved immediately, and a precipitate formed. The precipitate was filtered, washed with water, and dried under a stream of air to provide 2.34 g (13.4 mmol; 88%) of Compound 2 as a white solid.

Workup

  1. filtrationThe mixture was filtered through a plug of diatomaceous earth
  2. customreturned to a 0° C.
  3. additionwas slowly added
  4. customa precipitate formed
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried under a stream of air

Sources & evidence

ORD record
ord-8a72bdfdab11400abfb6efd22f8f41a8
Source dataset
uspto-grants-2007_01
Patent number
US07166628B2

Reaction notes

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