Hydrochloric Acid → Methyl 4-aminobenzenebutanoate

HRID 1264348

Reaction equation

HRID 1264348 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.Cl.[C:15]([O-])(O)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:15][O:12][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 270494-(4-Aminophenyl)butanoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 88628Methyl 4-aminobenzenebutanoateYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(4-aminophenyl)-butyric acid (5 g, 27.90 mmol) in MeOH (100 mL) at room temperature was added HCl conc. (37% 15 mL). The resulting mixture was stirred overnight at 50° C. then treated with a saturated aqueous solution NaHCO3 and Na2CO3 solid until pH 9. The solvent was evaporated under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The crude material was purified by flash chromatography using CH2Cl2/MeOH as solvent mixture yielding 40 (4.93 g, 91%) as orange solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe aqueous phase was extracted several times with CH2Cl2
  3. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-07b5adc5be564ca39d7e597a84da7449
Source dataset
uspto-grants-2003_04
Patent number
US06541661B1

Linked notes

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