Sodium Hydroxide → 2-amino-4-fluoro-N-methoxybenzamide

HRID 1045977Notes

Reaction equation

HRID 1045977 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])OC(=O)[NH:9][C:4]=2[CH:3]=1.Cl.[CH3:15][O:16][NH2:17].[OH-].[Na+]>CCOC(C)=O>[NH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:13]=[CH:12][C:5]=1[C:6]([NH:17][O:16][CH3:15])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 649746092-amino-4-fluoro-N-methoxybenzamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

NMR Spectrum: (DMSO-d6) 6.88 (dd, 1H), 7.21 (ddd, 1H), 8.00 (dd, 1H), 11.87 (s, 1H). 7-fluoro-1H-3,1-benzoxazine-2,4-dione (0.85 g, 4.69 mmol) was added to stirred solution of O-methylhydroxylamine hydrochloride (1.960 g, 23.47 mmol) in a 2N aqueous solution of sodium hydroxide (11.73 ml, 23.47 mmol) at 25° C. The resulting solution was stirred at room temperature for 2 hours. The solution was diluted with EtOAc, washed sequentially with water and brine. The organic layer was dried over magnesium sulfate and evaporated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM to afford 2-amino-4-fluoro-N-methoxybenzamide (0.390 g, 45.1%) as a white crystalline solid. NMR Spectrum: (DMSOd6) 3.67 (s, 3H), 6.30 (dd, 1H), 6.47 (ddd, 1H), 6.62 (bs, 2H), 7.37 (dd, 1H), 11.40 (s, 1H)

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-0111b59e6bf24f0d8c881685617e1734
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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