Sodium Hydroxide → Methyl 2-amino-4,6-dichlorobenzoate

HRID 1451295Notes

Reaction equation

HRID 1451295 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]2[C:10](=[O:15])[O:11][C:12](=O)[NH:13][C:8]=2[CH:7]=[C:6]([Cl:16])[CH:5]=1>CO>[NH2:13][C:8]1[CH:7]=[C:6]([Cl:16])[CH:5]=[C:4]([Cl:3])[C:9]=1[C:10]([O:11][CH3:12])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 123632155,7-dichloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 12363232Methyl 2-amino-4,6-dichlorobenzoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of sodium hydroxide (0.070 g, 1.8 mM) in methanol (8.5 mL) was added 5,7-dichloro-2H-3,1-benzoxazine -2,4(1H)-dione (4.13 g, 17.8 mM). The reaction mixture was stirred at 55° C. for 2 hr, allowed to cool to room temperature and concentrated. The residue was diluted with water and the resulting mixture extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered and concentrated to leave the methyl 2-amino-4,6-dichlorobenzoate (3.61 g, 92.1%) as a brown solid; MS(CI): 220 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. additionThe residue was diluted with water
  4. extractionthe resulting mixture extracted with ethyl acetate
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9d01085994754f41845ff54b0ebfd575
Source dataset
uspto-grants-1997_02
Patent number
US05604227

Reaction notes

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