1,2-Dichloroethane → 4-Amino-3-chlorobenzoic acid

HRID 51157

Reaction equation

HRID 51157 reaction equation
C(Cl)CCl.[NH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][C:7]=1[Cl:17]>CS(C)=O>[NH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[Cl:17]

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 1515285Ethyl 4-amino-3-chlorobenzoate2×

Product 1

HCID 172114-Amino-3-chlorobenzoic acidYield 112.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compound (1) (0.67 g, 5.5 mmol) and EDC (1.1 g, 5. 7 mmol) was dissolved in dimethyl sulfoxide (DMSO) (10 mL). N,N-dimethyl 1,2-ethylenediamine [compound (2)] (7.5 mL, 5.7 mmol) was added and the mixture was stirred at room temperature for 5 hours, whereafter the reaction mixture was freeze dried. The residue was subjected to column chromatography [silicon dioxide (SiO2) plates chromatographed in chloroform (CHCl3)-methanol (30:1, v/v)+triethylamine (Et3N) (1:1, v/v). This procedure gave quantitative yield (1.1 g) of compound (3) as a syrup.

Workup

  1. customdried
  2. customchromatographed in chloroform (CHCl3)-methanol (30:1

Sources & evidence

ORD record
ord-4b6b63a9481a46e09e5c7d107b9c9d63
Source dataset
uspto-grants-2004_03
Patent number
US06713517B1

Linked notes

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