Hydrochloric Acid → Methyl 4-(4-aminophenyl)butanoate hydrochloride

HRID 1168665Notes

Reaction equation

HRID 1168665 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[ClH:14].[CH3:15]O>>[ClH:14].[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:15])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 270494-(4-Aminophenyl)butanoic acid

Product 1

HCID 67161292Methyl 4-(4-aminophenyl)butanoate hydrochloride

Conditions

Temperature
85 °C

Procedure

4-(4-Aminophenyl)butyric acid (5 g) was dissolved in 40 ml methanol. The solution was refluxed at 80-90° C. with stirring for 4 h while hydrogen chloride gas was bubbled through the solution. After the reaction mixture was cooled to room temperature, ethyl ether (100 ml.) was added. The mixture, which separated into two layers, was refrigerated overnight. The crystalline product was collected by filtration and dried thoroughly. The filtrate was evaporated to dryness and the residue was recrystallized from MeOH/benzene. The total amount of the product methyl 4-(4-aminophenyl)butyrate hydrogen chloride obtained was 5.6 g (87.5%), m.p. 143-145° C.

Workup

  1. customwas bubbled through the solution
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. additionethyl ether (100 ml.) was added
  4. customThe mixture, which separated into two layers
  5. filtrationThe crystalline product was collected by filtration
  6. customdried thoroughly
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was recrystallized from MeOH/benzene

Sources & evidence

ORD record
ord-123d11850e324a729a5c541ce33068a6
Source dataset
uspto-grants-2003_09
Patent number
US06627228B1

Reaction notes

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