Hydrochloric Acid → 6-Amino-2-methyl-3-nitrobenzoic acid

HRID 22181

Reaction equation

HRID 22181 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:14]C(=O)C)=[C:8]([C:12]=1[CH3:13])[C:9]([OH:11])=[O:10])([O-:3])=[O:2].Cl>[OH-].[Na+]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:14])=[C:8]([C:12]=1[CH3:13])[C:9]([OH:11])=[O:10])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 152831716-Acetylamino-2-methyl-3-nitro-benzoic acid

Product 1

HCID 152831726-Amino-2-methyl-3-nitrobenzoic acidYield 48%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 10.2 g (43 mmoles) of 5-nitro-6-methyl-2-acetylaminobenzoic acid in 100 mL of 2M NaOH was heated to reflux for two hours. The resultant red solution was allowed to cool to near room temperature, then transferred to a beaker sitting in an ice bath. The solution was slowly acidified with 2N HCl to a pH of approximately 4-5 when a voluminous yellow solid separated out. In all, approximately 110 mL of 2N HCl was added. The collected yellow solid was dried in a vacuum oven for 3 hours at 75 degrees. 4.0 g (48% yield) 5-nitro-6-methyl-2-aminobenzoic acid was obtained. NMR(DMSO-d6): 2.45 (s,3H), 3.35(bs,2H), 6.68(d,1H,J=9.0 Hz), 7.86(d,1H,J=9.0 Hz). MS(m/z): 196(M+).

Workup

  1. temperatureto reflux for two hours
  2. customsitting in an ice bath
  3. customseparated out
  4. additionIn all, approximately 110 mL of 2N HCl was added
  5. customThe collected yellow solid was dried in a vacuum oven for 3 hours at 75 degrees

Sources & evidence

ORD record
ord-adeba882874f41c2af6f5027a5fb944a
Source dataset
uspto-grants-1995_06
Patent number
US05428021

Linked notes

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