Ammonium Acetate → 2-Amino-4-fluoro-5-iodo-3-methoxy-6-methylbenzamide

HRID 17292Notes

Reaction equation

HRID 17292 reaction equation
C([O-])(=O)C.[NH4+:5].[F:6][C:7]1[C:8]([I:22])=[C:9]([CH3:21])[C:10]2[C:15](=O)[O:14]C(=O)[NH:12][C:11]=2[C:18]=1[O:19][CH3:20]>CN(C)C=O>[NH2:12][C:11]1[C:18]([O:19][CH3:20])=[C:7]([F:6])[C:8]([I:22])=[C:9]([CH3:21])[C:10]=1[C:15]([NH2:5])=[O:14]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 866308067-Fluoro-6-iodo-8-methoxy-5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 860974202-Amino-4-fluoro-5-iodo-3-methoxy-6-methylbenzamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, ammonium acetate (4.62 g, 60.0 mmol) was added to an N,N-dimethylformamide (120 ml) solution of 7-fluoro-6-iodo-8-methoxy-5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (I-31) (4.2 g, 12.0 mmol), followed by stirring at room temperature for 16 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed three times with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was suspended in diisopropyl ether, followed by filtration and drying to obtain the entitled compound (3.74 g, 96%) as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed three times with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration under reduced pressure
  7. filtrationfollowed by filtration
  8. customdrying

Sources & evidence

ORD record
ord-6c3079e911ed4d9c859525c4f48c18e5
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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