N-(2-(benzyloxy)phenyl)-3-fluoroisonicotinamide → 3-fluoro-N-(2-hydroxyphenyl)isonicotinamide

HRID 718041Notes

Reaction equation

HRID 718041 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[F:23])C1C=CC=CC=1>Br.CC(O)=O.O.C(=O)(O)[O-].[Na+]>[F:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[OH:8])=[O:24]

Participants

6

Reactant 1

HCID 59783597N-(2-(benzyloxy)phenyl)-3-fluoroisonicotinamide

Product 1

HCID 597834993-fluoro-N-(2-hydroxyphenyl)isonicotinamideYield 75%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Title compound 24 (4.40 g, 13.6 mmol) was dissolved in 33% HBr in AcOH (30 mL) and the reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and solid sodium bicarbonate (until alkaline) then extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude was triturated in 30% ethyl acetate in hexanes to afford the title compound 25 (2.36 g, 75%) as a beige solid. LRMS (ESI): (calc) 232.06. (found) 233.1 (MH)+.

Workup

  1. extractionthen extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude was triturated in 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3df4b7fd99bc47faa230ce973e2eac64
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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