Water → 4,6-Dimethoxyisatoic anhydride

HRID 272629Notes

Reaction equation

HRID 272629 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>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[NH:14][C:16](=[O:18])[O:9][C:7](=[O:8])[C:6]2=[C:10]([O:12][CH3:13])[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), [Newman, H.; Angier, R. B. J. Org. Chem., 1969, 34(11), 3484] in THF (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 cold (0° C.) water (4 L). Additional water (2 L) 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 4,6-dimethoxyisatoic anhydride.

Workup

  1. stirringstirring of the thick solid
  2. customformed
  3. stirringAfter stirring for 30 min
  4. filtrationthe reaction mixture was filtered
  5. customto give a beige solid
  6. washThe solid was washed with water
  7. customair-dried
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-c87dab74a2e648f9a97b6506f61d4165
Source dataset
uspto-grants-2008_11
Patent number
US07456188B1

Reaction notes

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