Ammonia → 2-Amino-3-chlorobenzoic acid

HRID 2253933Notes

Reaction equation

HRID 2253933 reaction equation
Cl[C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].[NH3:14]>Cl[Cu].O>[NH2:14][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 57652,3-Dichlorobenzoic acidHCID 14798Sodium Hydroxide

Product 1

HCID 808072-Amino-3-chlorobenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution comprising 191 parts of 2,3-dichlorobenzoic acid and 40 parts of NaOH prills in 500 parts of water, and 3 parts of CuCl are initially introduced into a 2 l V4A autoclave. 425 parts of liquid NH3 (d20 : 0.61) are then also forced in, and the autoclave is heated at 165° to 175° C. for 3 hours, during which the pressure drops from initially 50 bar to about 46 bar. When the reaction has ended, the contents of the autoclave are cooled to 25° C. and drained off over the ascending line. The reaction solution is boiled under reflux until a bottom temperature of 100° C. is reached, and the NH3 gas driven off is collected in a waste gas washer. Working up in accordance with Example 1 gives 168 parts (98% of theory) of 2-amino-3-chlorobenzoic acid of melting point 185° to 187 ° C.

Workup

  1. additionare initially introduced into a 2 l V4A autoclave
  2. temperatureis heated at 165° to 175° C. for 3 hours, during which the pressure
  3. temperatureunder reflux until a bottom temperature of 100° C.
  4. customis collected in a waste gas washer

Sources & evidence

ORD record
ord-f2f4c557cc7a470095cfa89b965897c6
Source dataset
uspto-grants-1993_08
Patent number
US05233083

Reaction notes

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