Methyl 4-amino-3,5-dichlorobenzoate → 2,6-Dichloroaniline

HRID 1885705Notes

Reaction equation

HRID 1885705 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[NH2:12])C(OC)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:9]=[C:10]([Cl:13])[C:11]=1[NH2:12]

Participants

3

Reactant 1

HCID 604808Methyl 4-amino-3,5-dichlorobenzoate

Product 1

HCID 118462,6-DichloroanilineYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
250 °C

Procedure

0.2 mole=48 g of methyl 3,5-dichloro-4-amino-benzoate were initially introduced into an autoclave together with 250 ml of water. The mixture was heated to 250° C. and stirred at this temperature for 3 hours. Reaction gas formed was continuously let off to maintain a pressure of about 40 bar. The product was recovered by steam distillation. 26.9 g of 2,6-dichloroaniline were obtained, corresponding to a yield of 75.3%.

Workup

  1. customReaction gas
  2. customformed
  3. temperatureto maintain a pressure of about 40 bar
  4. distillationThe product was recovered by steam distillation

Sources & evidence

ORD record
ord-a3e97fd4f2cf4440b099c05a31a7bead
Source dataset
uspto-grants-1992_09
Patent number
US05145958

Reaction notes

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