Trifluoroacetic acid → 3-Amino-N-(4-chlorophenyl)pyridine-4-carboxamide

HRID 1787887Notes

Reaction equation

HRID 1787887 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:16])=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:16]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 576024633-(N-tert-Butoxycarbonylamino)-N-(4-chlorophenyl)-pyridine-4-carboxamide

Product 1

HCID 183767043-Amino-N-(4-chlorophenyl)pyridine-4-carboxamideYield 93.2%

Procedure

To 3-(N-tert-butoxycarbonylamino)-N-(4-chlorophenyl)-pyridine-4-carboxamide (552 mg, 1.59 mmol) was added trifluoroacetic acid (3 mL, 38.95 mmol). After stirring for 10 min, the reaction mixture was concentrated, diluted with CH2Cl2, washed with satd Na2CO3, dried (Na2SO4) and concentrated to give the title compound (367 mg, 93%) as a pale yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with CH2Cl2
  3. washwashed with satd Na2CO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c0ec90aa0e64da095384d499776ad82
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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