Anthranilic Acid → 2-Azidobenzoic acid

HRID 1991480Notes

Reaction equation

HRID 1991480 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[N-:20]=[N+:21]=[N-].[Na+]>Cl.O.O1CCOCC1.CO>[N:4]([C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])=[N+:20]=[N-:21]

Participants

9

Reactant 4

HCID 227Anthranilic AcidHCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 53255602-Azidobenzoic acidYield 58%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

Anthranilic acid (12.3 g, 90 mmol) was dissolved in a mixture of aqueous HCl (36%, 50 mL), H2O (100 mL), dioxane (50 mL) and methanol (50 mL) at 0° C. and treated dropwise with NaNO2 (7.6 g, 110 mmol) dissolved in H2O (50 ml) whereas the temperature of the reaction mixture was kept below 5° C. After 1 h at 0° C. the mixture was poured onto an icy solution of sodium acetate (26 g, 317 mmol) and sodium azide (15 g, 230 mmol) in ca. 300 ml of water. Repeated (ca. 3 times) extraction of the resulting suspension with ethylacetate, drying of the combined organic phases, and evaporation of the solvent gave (8.5 g, 58%) of 2-azido-benzoic acid. MS (ES+): 164 (M+H).

Workup

  1. customwas kept below 5° C
  2. extraction(ca. 3 times) extraction of the resulting suspension with ethylacetate
  3. customdrying of the combined organic phases, and evaporation of the solvent

Sources & evidence

ORD record
ord-04851451eccb42848832809c7fd70205
Source dataset
uspto-grants-2010_01
Patent number
US07645785B2

Reaction notes

Loading…