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

HRID 581832Notes

Reaction equation

HRID 581832 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH3:17]O>>[ClH:3].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=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

12.96 g (0.11 mol) of thionyl chloride (7.93 ml) are added dropwise to a solution of 15 g (0.0991 mol) of 3-(4-amino-phenyl)-propionic acid in 100 ml of methanol, while stirring and cooling with methanol/ice. When the addition has ended, the mixture is stirred for a further 30 minutes, while cooling, and is then stirred overnight at room temperature. It is then concentrated to dryness in vacuo and the residue is crystallized from methanol/ether.

Workup

  1. additionWhen the addition
  2. stirringthe mixture is stirred for a further 30 minutes
  3. temperaturewhile cooling
  4. stirringis then stirred overnight at room temperature
  5. concentrationIt is then concentrated to dryness in vacuo
  6. customthe residue is crystallized from methanol/ether

Sources & evidence

ORD record
ord-2f3921ca1aef42559aea1d71da11bc71
Source dataset
uspto-grants-1999_07
Patent number
US05922717

Reaction notes

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