Reaction #902

ord-36a2a540166a44e2ae3ef4e91516ef3a

Reaction equation

CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O
2-methyl-3-nitro-6-acetamidobenzoic acid
Cl
HCl
→
Cc1c([N+](=O)[O-])ccc(N)c1C(=O)O
2-Methyl-3-nitro-6-aminobenzoic acid

Reactants

CC(=O)Nc1ccc([N+](=O)[O-])c(C)c1C(=O)O
2-methyl-3-nitro-6-acetamidobenzoic acid
Cl
HCl

Reagents

None

Solvents

[Na+].[OH-]
NaOH

Conditions

Temperature
95°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling to 10° C.
  2. 2
    Filtrationthe precipitate which deposits is filtered off with suction
  3. 3
    Washwashed with water
  4. 4
    Otherdried under reduced pressure at 50° C.

Procedure

450 ml of 2N NaOH are initially taken and 75.6 g (0.317 mol) of 2-methyl-3-nitro-6-acetamidobenzoic acid are added. The reaction mixture is then warmed to 95° C. and is stirred at this temperature for one hour. After cooling to 10° C., it is acidified by addition of 425 ml of 2N HCl, 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