1-Aminocyclopropane-1-carboxylic acid → Ethyl 1-aminocyclopropane-1-carboxylate hydrochloride

HRID 246706

Reaction equation

HRID 246706 reaction equation
[NH2:1][C:2]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3]1.S(Cl)([Cl:10])=O.[CH2:12](O)[CH3:13]>>[ClH:10].[NH2:1][C:2]1([C:5]([O:7][CH2:12][CH3:13])=[O:6])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 702EthanolHCID 24386Thionyl Chloride

Product 1

HCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideYield 100%

Conditions

Temperature
0 °C

Procedure

A suspension of 1-aminocyclopropanecarboxylic acid (5.8 g, 57.4 mmol) in 300 mL of ethanol was cooled to 0° C., thionyl chloride (20.5 g, 172.7 mmol) was added drop-wise over 30 minutes. Then the cold bath was removed and the reaction mixture was heated at reflux for 2 hours, then the mixture was stirred at room temperature for 16 hours. The solvent was evaporated at 40° C. under reduced pressure to give ethyl 1-aminocyclopropanecarboxylate hydrochloride (9.53 g, 100%) as a solid. It was used directly in the next step without further purification. MS: (M+H)+=130.2; 1H NMR (300 MHz, DMSO): δ 9.04 (brs, 3H), 4.14 (q, 2H, J=6.9 Hz), 1.45 (d, 2H, J=3.3 Hz), 1.37 (d, 2H, J=3.2 Hz), 1.19 (t, 3H, J=6.9 Hz).

Workup

  1. customThen the cold bath was removed
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 2 hours
  4. customThe solvent was evaporated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-dd1342184d5548d2935f6b562c20a59e
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

Loading…