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

HRID 1421304Notes

Reaction equation

HRID 1421304 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) δ 9.32 (br s, 3 H), 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)δ 168.8, 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-c895b08ee021430db5716b2a8de8ba44
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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