Diethyl Ether → 4-(2-Aminoethyl)-2-chlorophenol

HRID 14845

Reaction equation

HRID 14845 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.S(Cl)([Cl:15])(=O)=O.CCOCC>C(O)(=O)C>[NH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[C:4]([Cl:15])[CH:5]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4657O-MethyltyramineHCID 24648Sulfuryl chloride

Product 1

HCID 230715554-(2-Aminoethyl)-2-chlorophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.1 mol of 2-(4-Methoxy-phenyl)-ethylamine was dissolved in 200 ml of acetic acid, followed by addition of 1.5 eq. of sulfuryl chloride at 0° to 5° C. The solution was stirred at room temperature for 1 hour. 250 ml of ether was added and the resulted solid was collected by filtration. The solid was heated in 48% aqueous HBr at 135° C. for 4 hours, cooled to 0° C., and the crystal was collected by filtration and washed with small amount of methanol then with ethyl acetate. LC-MS showed the product as HBr salt had the expected M+H+ of 186. 1H NMR (Varian 300 MHz, CD3OD shifts relative to the solvent peak at 3.3 ppm) δ 7.2 (d, 1H) 7.0 (m, 1H) 6.9 (d, 1H) 3.1 (m, 2H) 2.9 (m, 2H).

Workup

  1. filtrationthe resulted solid was collected by filtration
  2. temperatureThe solid was heated in 48% aqueous HBr at 135° C. for 4 hours
  3. temperaturecooled to 0° C.
  4. filtrationthe crystal was collected by filtration
  5. washwashed with small amount of methanol

Sources & evidence

ORD record
ord-f642b3d2bd1945ed90836493516f8c34
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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