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

HRID 3104Notes

Reaction equation

HRID 3104 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-739ac2ee85f042ce86c3862c763ac88d
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Reaction notes

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