Hydrochloric Acid → 2-Amino-4-chloro-5-methylbenzoic acid

HRID 47848Notes

Reaction equation

HRID 47848 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:9]#N)=[C:6]([CH:8]=1)[NH2:7].[OH-:12].[K+].[OH:14]O.Cl>O>[NH2:7][C:6]1[CH:8]=[C:2]([Cl:1])[C:3]([CH3:11])=[CH:4][C:5]=1[C:9]([OH:14])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 108558652-Amino-4-chloro-5-methylbenzonitrile

Product 1

HCID 110953002-Amino-4-chloro-5-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-cyano-4-methylaniline (4.0 g,0.024 mol), 30% aqueous KOH solution (56 ml), and 30% hydrogen peroxide (4 ml) was placed in an oil bath preheated to 130° C., then stirred at this temperature for 2 hours (a clear solution had obtained after 1.5 h). The clear solution was then allowed to cool to room temperature, diluted with water (200 ml), and acidified to pH ˜5.50 with 3N HCl, then allowed to stand at room temperature for few hours. The off white solid was collected by filtration, washed with water and dried in vacuo over P2O5 (4.13 g, 93%), mp 212-215° C. 1H-NMR (DMSO-d6) 2.16 (s, 3H, CH3), 6.83, 7.62 (2×s, 2H, 3-H, 6-H), 8.50 (br s, 2H, NH2); MS (FAB, m/z): 188, 186 (M+H)+; FAB-HRMS: measured: 185.0256; calculated for C8H8ClNO2 (M+) 185.0244.

Workup

  1. customwas placed in an oil bath
  2. custompreheated to 130° C.
  3. customhad obtained after 1.5 h)
  4. waitto stand at room temperature for few hours
  5. filtrationThe off white solid was collected by filtration
  6. washwashed with water
  7. dry with materialdried in vacuo over P2O5 (4.13 g, 93%), mp 212-215° C

Sources & evidence

ORD record
ord-0fda456ece1346fb83b3a6d08010dd28
Source dataset
uspto-grants-2004_03
Patent number
US06699861B1

Reaction notes

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