Hydrochloric Acid → Methyl 4-amino-3-(trifluoromethoxy)benzoate

HRID 1749453Notes

Reaction equation

HRID 1749453 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].Cl.O1CCOC[CH2:18]1>CO>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:13])([F:14])[F:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 27359514-amino-3-(trifluoromethoxy)benzoic Acid

Product 1

HCID 53419671Methyl 4-amino-3-(trifluoromethoxy)benzoateYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-amino-3-(trifluoromethoxy)benzoic acid (8.88 g 40.2 mmol), MeOH (142 mL) and hydrochloric acid in 1,4-dioxane (4.0 M, 142 mL, 568 mmol) was stirred at room temperature for 72 h. After removal of the organic solvent the pH of the residue was adjusted to pH 8 and the aqueous layer was extracted with ethyl acetate (50 mL×3). The combined organic layers were dried and concentrated under vacuum to afford the title compound (9.3 g, 39.6 mmol, 95% yield). MS (ESI) m/z 236.1 [M+1]+.

Workup

  1. customAfter removal of the organic solvent the pH of the residue
  2. extractionthe aqueous layer was extracted with ethyl acetate (50 mL×3)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6396414582c348febe03944f4c49377b
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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