Ethanol → Ethyl 2-amino-5-(trifluoromethyl)benzoate

HRID 42039Notes

Reaction equation

HRID 42039 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=O)(C)(C)C.OS(O)(=O)=O.[CH2:27](O)[CH3:28]>>[NH2:8][C:9]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][C:10]=1[C:11]([O:13][CH2:27][CH3:28])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 150338862-((tert-Butoxycarbonyl)amino)-5-(trifluoromethyl)benzoic acid

Product 1

HCID 54208492Ethyl 2-amino-5-(trifluoromethyl)benzoateYield 41%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(tert-butoxycarbonylamino)-5-(trifluoromethyl)benzoic acid (7.21 mmol, 2.2 g), H2SO4 (36 mmol, 1.92 ml) in ethanol (25 ml) was stirred at 100° C. for 16 hours. The solvent was evaporated, water was added, pH was taken to 6 and extracted with CHCl3. The crude mixture was purified by chromatography over SiO2 eluting with DCM/MeOH mixtures and affording 0.69 g (yield 41%) of the expected product.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionextracted with CHCl3
  4. customThe crude mixture was purified by chromatography over SiO2 eluting with DCM/MeOH mixtures

Sources & evidence

ORD record
ord-e30161a12a854bb5a83611441302d0d4
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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