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

HRID 480296Notes

Reaction equation

HRID 480296 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-4d17a66d885547a090c417d470ff5639
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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