Hydrochloric Acid → 3-amino-4-(methylcarbamoyl)benzoic Acid

HRID 1451115Notes

Reaction equation

HRID 1451115 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH:14][CH3:15])=[O:13])[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH:14][CH3:15])=[O:13])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10798400Methyl 3-amino-4-(methylcarbamoyl)benzoate

Product 1

HCID 104201413-amino-4-(methylcarbamoyl)benzoic AcidYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 3-amino-4-(methylamino)carbonylbenzoate (0.624 g, 0.003 mol) and 1N sodium hydroxide (4.5 mol, 0.0045 mol) was stirred at room temperature for 4 h. The mixture was neutralized with concentrated hydrochloric acid and then acetic acid was added to bring the pH close to 3. The precipitate obtained was collected by filtration, washed with water, and dried under vacuum over acetone for 24 h to give 0.4 g (69%) of 3-amino-4-(methylamino)carbonylbenzoic acid as a pale yellow powder, mp 215°-217° C.

Workup

  1. customclose to 3
  2. customThe precipitate obtained
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. dry with materialdried under vacuum over acetone for 24 h

Sources & evidence

ORD record
ord-2c6a40e6e46944d48ca1a4586a668851
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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