Hydrochloric Acid → 2-Acetamido-6-methylbenzoic acid

HRID 1599968Notes

Reaction equation

HRID 1599968 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].[OH-].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15].Cl>O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH:11][C:14](=[O:16])[CH3:15])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 1512106-Methylanthranilic acid

Product 1

HCID 28014002-Acetamido-6-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

90.6 g (0.6 mol) of 6-methylanthranilic acid is added to a solution of 24.8g (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 waterand dried under reduced pressure at 50° C. Yield: 107 g (0.55 mol)=92% of theory, m.p.: 189°-190° C.

Workup

  1. additionare then added dropwise
  2. temperaturewith cooling
  3. filtrationthe precipitate which deposits is filtered off with suction
  4. washwashed with waterand
  5. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-eb2a0f8dd5584641be5cd1f4ade554b7
Source dataset
uspto-grants-1998_04
Patent number
US05744425

Reaction notes

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