Hydrogen Peroxide → Methyl 2-amino-3,5-dichlorobenzoate

HRID 1105940

Reaction equation

HRID 1105940 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([Cl:14])[CH:13]=1)[NH:10]C(=O)C2=O.OO.[CH3:19][OH:20]>>[Cl:14][C:12]1[CH:13]=[C:5]([Cl:4])[CH:6]=[C:7]([C:1]([O:20][CH3:19])=[O:2])[C:11]=1[NH2:10]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 887Methanol2×HCID 807715,7-Dichloro-1H-indole-2,3-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 613050Methyl 2-amino-3,5-dichlorobenzoateYield 80%

Procedure

20 parts of a 30 percent strength by weight solution of sodium methylate in methanol are added to 21.6 parts of 5,7-dichloroisatin in 300 parts of methanol at -10° C., resulting in a dark violet suspension of a bulky precipitate. 7 parts of 50 percent strength by weight hydrogen peroxide solution are then added at -3° C. and thereafter the mixture is stirred for one hour at room temperature. The solution is concentrated and the crystalline residue is mixed with water and filtered off. 17.6 parts (80% of theory) of methyl 3,5-dichloroanthranilate, of melting point 62°-63° C., are obtained.

Workup

  1. customresulting in a dark violet suspension of a bulky precipitate
  2. concentrationThe solution is concentrated
  3. additionthe crystalline residue is mixed with water
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-712ebecaa0a444e9aa292ba03bb35d3e
Source dataset
uspto-grants-1982_01
Patent number
US04310677

Linked notes

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