Hydrochloric Acid → Ethyl 4-(4-aminophenyl)butanoate

HRID 1595851Notes

Reaction equation

HRID 1595851 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=1.Cl.[CH3:20][CH2:21]O>>[CH2:20]([O:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([NH2:6])=[CH:12][CH:11]=1)[CH3:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1118Sulfuric AcidHCID 270494-(4-Aminophenyl)butanoic acid

Product 1

HCID 10013251Ethyl 4-(4-aminophenyl)butanoate

Procedure

Catalytic sulfuric acid was added to a solution of 4-(4-aminophenyl) butyric acid (6.0 g, 33.48 mmol) in EtOH. The reaction mixture was stirred at room temperature for 24 h. HCl (5 mL, 6N) was added and the reaction mixture was heated at reflux for 24 h. The reaction mixture was concentrated in vacuo and CH2Cl2 and water were added. The pH was adjusted to 7.0 with aqueous NaHCO3 (satd). The organic solution was washed with water (1×) and brine (1×), dried over MgSO4, filtered, and concentrated to afford 4-(4-amino-phenyl)-butyric acid ethyl ester (1.53 g). 1H NMR (400 MHz, CDCl3) δ 6.95 (d, 2H), 6.61 (d, 2H), 4.10 (q, 2H), 3.66 (bs, 2H), 2.53 (t, 2H), 2.29 (t, 2H), 1.88 (m, 2H), 1.24 (t, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. concentrationThe reaction mixture was concentrated in vacuo and CH2Cl2 and water
  4. additionwere added
  5. washThe organic solution was washed with water (1×) and brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1b9e9921ae0440e2b5f6ba3a0cdc3906
Source dataset
uspto-grants-2001_09
Patent number
US06288120B1

Reaction notes

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