Trifluoroacetic acid → 2-Chloro-3,5-Dimethoxyaniline

HRID 1783548

Reaction equation

HRID 1783548 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[C:9]=1[Cl:18])(C)(C)C.FC(F)(F)C(O)=O>>[Cl:18][C:9]1[C:10]([O:16][CH3:17])=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=1[NH2:7]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54265450HCID 54265450, compound

Product 1

HCID 227430742-Chloro-3,5-DimethoxyanilineYield 101,012.797%

Procedure

To 6.01 g (0.021 mmol) of (2-chloro-3,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester was added 15 mL of trifluoroacetic acid. The reaction was stirred for 3 hours at room temperature, then concentrated in vacuo. The residue was made basic with a saturated solution of sodium bicarbonate, then extracted three times with dichloromethane. The combined dichloromethane layers were dried with magnesium sulfate and concentrated in vacuo to give 3.98 g of the title compound, which was used as is in the following example.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined dichloromethane layers were dried with magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7d2e9ad817e419e9dccae79ac1fec04
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Linked notes

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