Reaction #900

ord-1754134a9e1b4ab5a610540df5e81abc

Reaction equation

Cl
HCl
Cc1cccc(N)c1C(=O)O
6-methylanthranilic acid
[Na+].[OH-]
NaOH
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)Nc1cccc(C)c1C(=O)O
2-Methyl-6-acetamidobenzoic acid

Reactants

Cl
HCl
Cc1cccc(N)c1C(=O)O
6-methylanthranilic acid
[Na+].[OH-]
NaOH
CC(=O)OC(C)=O
acetic anhydride

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONare then added dropwise
  2. 2
    Temperaturewith cooling
  3. 3
    Filtrationthe precipitate which deposits is filtered off with suction
  4. 4
    Washwashed with water
  5. 5
    Otherdried under reduced pressure at 50° C.

Procedure

90.6 g (0.6 mol) of 6-methylanthranilic acid are added to a solution of 24.8 g (0.62 mol) of NaOH in 500 ml of water and 63.4 g (0.62 mol) of acetic anhydride are then added dropwise. After stirring for one hour, the mixture is acidified to pH 3 with conc. HCl with cooling, and the precipitate which deposits is filtered off with suction, washed with water and dried under reduced pressure at 50° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723415uspto-grants-1998_03