Trifluoroacetic acid → 4-(2-Methoxy-4-(methylamino)-5-nitrophenoxy)pyridine-2-carboxylic acid

HRID 30807Notes

Reaction equation

HRID 30807 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:29]=[C:28]([NH:30][CH3:31])[C:27]([N+:32]([O-:34])=[O:33])=[CH:26][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21]C(C)(C)C)=[O:20])[CH:14]=1>>[CH3:8][O:9][C:10]1[CH:29]=[C:28]([NH:30][CH3:31])[C:27]([N+:32]([O-:34])=[O:33])=[CH:26][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69003260HCID 69003260, compound

Product 1

HCID 690019044-(2-Methoxy-4-(methylamino)-5-nitrophenoxy)pyridine-2-carboxylic acid

Procedure

Trifluoroacetic acid was added neat to tert-butyl 4-(2-methoxy-4-(methylamino)-5-nitrophenoxy)pyridine-2-carboxylate and stirred at room temperature for 5 hours. TFA was evaporated, solid product azeotroped with toluene then placed under vacuum for 24 hours to yield 4-(2-methoxy-4-(methylamino)-5-nitrophenoxy)pyridine-2-carboxylic acid. HPLC=3.07 min; MS: MH+=321

Workup

  1. customTFA was evaporated
  2. customsolid product azeotroped with toluene
  3. waitthen placed under vacuum for 24 hours

Sources & evidence

ORD record
ord-d5312eb3bf7841778acad0c0a26e08f9
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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