Methanol → Methyl 3-(4-aminophenyl)propanoate--hydrogen chloride (1/1)

HRID 1940521Notes

Reaction equation

HRID 1940521 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O.[CH3:17]O>>[ClH:15].[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:17])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 754513-(4-Aminophenyl)propionic acid

Product 1

HCID 24191581Methyl 3-(4-aminophenyl)propanoate--hydrogen chloride (1/1)

Procedure

A solution of 15 g (0.0991 Mol) of 3-(4-amino-phenyl)-propionic acid in 100 ml methanol is combined dropwise with 12.96 g (0.11 Mol) of thionyl chloride (7.93 ml) with stirring and cooling with methanol/ice. After it has all been added, the mixture is stirred for a further 30 minutes and then overnight at ambient temperature. It is then evaporated to dryness in vacuo and the residue is crystallised from methanol/ether.

Workup

  1. additionall been added
  2. stirringthe mixture is stirred for a further 30 minutes
  3. customovernight
  4. customat ambient temperature
  5. customIt is then evaporated to dryness in vacuo
  6. customthe residue is crystallised from methanol/ether

Sources & evidence

ORD record
ord-8c5b1375ab384971a61f3c9788aac5fa
Source dataset
uspto-grants-1997_12
Patent number
US05700801

Reaction notes

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