Acetic Acid → 2-Amino-5-Chloro-N,3-Dimethylbenzamide

HRID 490971Notes

Reaction equation

HRID 490971 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[NH:10]C(=O)[O:8][C:7](=O)[C:6]=2[CH:13]=1.C(O)(=O)C.[CH3:19][NH2:20].O>C(#N)C>[NH2:10][C:5]1[C:4]([CH3:14])=[CH:3][C:2]([Cl:1])=[CH:13][C:6]=1[C:7]([NH:20][CH3:19])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6329MethylamineHCID 115502595-Chloro-3-methyl isatoic anhydride

Product 1

HCID 250682512-Amino-5-Chloro-N,3-DimethylbenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 6-chloro-8-methyl-2H-3,1-benzoxazine-2,4(1H)-dione (211.6 g, 1000 mmol) in acetonitrile (700 mL) was added acetic acid (7.3 g, 122 mmol). Then 40% aqueous methylamine (104 mL) was added dropwise over 30 minutes at 25-30° C. Stirring was continued for 2 h, and then water (700 mL) was added slowly. The resulting suspension was cooled to 5° C., and stirred for 30 minutes at this temperature. The suspension was then filtered, and the solids were washed with water (3×200 mL) and dried under nitrogen to afford the title compound as off-white needles, 172.8 g (87.0% yield), m.p. 141-143° C.

Workup

  1. stirringstirred for 30 minutes at this temperature
  2. filtrationThe suspension was then filtered
  3. washthe solids were washed with water (3×200 mL)
  4. customdried under nitrogen

Sources & evidence

ORD record
ord-ebbb23c7f0d44b34bf244cb2203da18f
Source dataset
uspto-grants-2009_05
Patent number
US07528260B2

Reaction notes

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