Phosgene → 5-Methylisatoic anhydride

HRID 635510Notes

Reaction equation

HRID 635510 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[C:12](Cl)(Cl)=[O:13]>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[C:6]2[C:7]([O:9][C:12](=[O:13])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 2944785-Methylisatoic anhydrideYield 83.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 10.0 g (66.0 mmol) of 5-methylanthranilic acid in 60 mL of 1,4-dioxane was slowly added 100 mL (193 mmol) of a 1.93 molar solution of phosgene in toluene, at room temperature. The mixture was stirred overnight at room temperature, followed by concentration in vacuo to a small volume. The concentrated reaction mixture was filtered through silica and the filter cake was washed with hexane to give 9.81 g (83.7%) of the 5-methylisatoic anhydride as a light yellow solid. MS (Cl mode) m/z 160 (M-18, 100%), 178 (M+H, 71%).

Workup

  1. customat room temperature
  2. concentrationfollowed by concentration in vacuo to a small volume
  3. customThe concentrated reaction mixture
  4. filtrationwas filtered through silica
  5. washthe filter cake was washed with hexane

Sources & evidence

ORD record
ord-8e0c188a5b3643b79df9b9ebd6e5c176
Source dataset
uspto-grants-2001_02
Patent number
US06187923B1

Reaction notes

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