Methanol → Methyl 2-amino-5-(trifluoromethyl)benzoate

HRID 2203149Notes

Reaction equation

HRID 2203149 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:20]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:20])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 104655352-Amino-5-(trifluoromethyl)benzoic acid

Product 1

HCID 14233808Methyl 2-amino-5-(trifluoromethyl)benzoateYield 51%

Conditions

Temperature
125 °C

Procedure

A solution of 2-amino-5-(trifluoromethyl)benzoic acid (1.07 g, 5.2 mmoles) in methanol (20 ml) was treated with concentrated sulphuric acid (0.5 ml) and heated under microwave conditions at 125° C. for 2 h. The mixture was evaporated to dryness and treated with water (100 ml) then basified to saturation with potassium carbonate and extracted with ethyl acetate (2×40 ml). The combined extracts were dried over sodium sulphate, filtered and evaporated to dryness. The residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient. This gave the title compound 1 as a colorless oil (0.59 g, 51%).

Workup

  1. customThe mixture was evaporated to dryness
  2. additiontreated with water (100 ml)
  3. extractionextracted with ethyl acetate (2×40 ml)
  4. dry with materialThe combined extracts were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-f1afce9e51e148108e6d89fbc216197b
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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