Ethanol → 3-Pyridinepropanoic acid, β-amino-, ethyl ester, hydrochloride (1:1)

HRID 1940072Notes

Reaction equation

HRID 1940072 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][CH:6]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:7][C:8]([OH:10])=[O:9].[CH2:17](O)[CH3:18]>>[ClH:3].[NH2:5][CH:6]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:7][C:8]([O:10][CH2:17][CH3:18])=[O:9]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 36065473-Amino-3-(pyridin-3-yl)propanoic acid

Product 1

HCID 183230693-Pyridinepropanoic acid, β-amino-, ethyl ester, hydrochloride (1:1)Yield 79%

Procedure

To 40 mL of stirred ethanol at 0° C. under nitrogen was slowly added thionyl chloride (3.3 mL, 45 mmol) followed by addition of 3-amino-3-(3-pyridyl)propionic acid (2.65 g, 15 mmol). The reaction mixture was allowed to slowly warm to room temperature and then refluxed for 3 hours. After 2 hours at reflux all of the solid had dissolved. The reaction mixture was allowed to cool to room temperature and stirred overnight. The slurry was filtered and the solid was washed with copious amounts of ethanol. The solid was dried in vacuo (60° C., <1 mm) to afford 3.17 g (79%) of ethyl 3-amino-3-(3-pyridyl)propionate hydrochloride as a white powder: 1H NMR (DMSO-d6, 250 MHz) δ9.32 (br s, 3H), 9.21 (br s, 1H), 8.87-8.95 (m, 2H), 8.09-8.14 (m, 1H), 4.93 (br s, 1H), 3.90-4.15 (m, 2H), 3.20-3.38 (m, 2H), 1.11 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ168.8, 144.5, 142.8, 142.6, 136.2, 126.7, 60.7, 47.9, 37.2, 13.9.

Workup

  1. customat 0° C.
  2. temperaturerefluxed for 3 hours
  3. temperatureAfter 2 hours at reflux all of the solid
  4. dissolutionhad dissolved
  5. temperatureto cool to room temperature
  6. filtrationThe slurry was filtered
  7. washthe solid was washed with copious amounts of ethanol
  8. customThe solid was dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-cb0483d3c8f8407691a50d1fef358705
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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