2-((tert-Butoxycarbonyl)amino)-5-(trifluoromethoxy)benzoic acid → 2-amino-5-(trifluoromethoxy)benzoic Acid

HRID 1270789Notes

Reaction equation

C([NH:8][C:9]1[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(OC(C)(C)C)=O>O1CCOCC1>[F:20][C:19]([F:21])([F:22])[O:18][C:15]1[CH:14]=[C:10]([C:11]([OH:13])=[O:12])[C:9]([NH2:8])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The above benzoic acid (120 g, 0.37 mol) is suspended in 1,4-dioxane (200 mL), stirred and warmed to 80° C. until dissolved. The solution is allowed to cool to room temperature and hydrogen chloride is bubbled into the reaction mixture for 30 minutes. Stirring is continued for 2 hours, during which time a precipitate forms. The precipitate is collected and washed with ice-cold water (1000 mL) and Et2O (500 mL) to give 5-trifluoromethoxyanthranilic acid as a solid.

Workup

dissolutionuntil dissolved
temperatureto cool to room temperature
customhydrogen chloride is bubbled into the reaction mixture for 30 minutes
stirringStirring
customThe precipitate is collected
washwashed with ice-cold water (1000 mL) and Et2O (500 mL)

Sources & evidence

ORD record: ord-794df99dcc324112aff9a421c2cb406e
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202364B2

Reaction notes

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