Water → 4,6-Dimethoxyisatoic anhydride

HRID 130326Notes

Reaction equation

HRID 130326 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:14])[C:6](=[C:10]([O:12][CH3:13])[CH:11]=1)[C:7]([OH:9])=[O:8].Cl[C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl.O>O1CCCC1>[CH3:13][O:12][C:10]1[C:6]2[C:7](=[O:9])[O:8][C:16](=[O:18])[NH:14][C:5]=2[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 94429TriphosgeneHCID 116584562-Amino-4,6-dimethoxybenzoic acid

Product 1

HCID 116010104,6-Dimethoxyisatoic anhydrideYield 262.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) brown solution of 4,6-dimethoxy anthranilic acid (76.0 g, 0.385 mol), prepared as in Example 2, in tetrahydrofuran (1.3 L) was added triphosgene (40.0 g, 0.135 mol) in portions over a 20 min period. After 30 min, the reaction was warmed to room temperature and stirred for an additional 1.5 h. The reaction mixture was poured into an Erlenmeyer flask containing water and cooled to 0° C. with an ice bath. Additional water was added to facilitate the stirring of the thick solid formed. After stirring for 30 min, the reaction mixture was filtered to give a beige solid. The solid was washed with water, air-dried, and then dried under high vacuum to give 79.2 g (92%) of the isatoic anhydride.

Workup

  1. temperatureTo a cooled
  2. additionThe reaction mixture was poured into an Erlenmeyer flask
  3. temperaturecooled to 0° C. with an ice bath
  4. stirringstirring of the thick solid
  5. customformed
  6. stirringAfter stirring for 30 min
  7. filtrationthe reaction mixture was filtered
  8. customto give a beige solid
  9. washThe solid was washed with water
  10. customair-dried
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-806e20c2ebcb41a887e211376dfeb163
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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