ChemicalBook CAS DataBase List 1-Aminocyclopropane-1-carboxylic acid hydrochloride

1-Aminocyclopropane-1-carboxylic acid hydrochloride synthesis

7synthesis methods

Product Name:1-Aminocyclopropane-1-carboxylic acid hydrochloride
CAS Number:68781-13-5
Molecular formula:C4H8ClNO2
Molecular Weight:137.5648

methyl 1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)cyclopropanecarboxylate

109541-75-5
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1-Aminocyclopropane-1-carboxylic acid hydrochloride

68781-13-5
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Yield:68781-13-5 95%

Reaction Conditions:

with hydrogenchloride in water for 8 h;Reflux;

Steps:

1-Aminocyclopropanecarboxylic Acid Hydrochloride (4·HCl)
Phthalimidocyclopropanecarboxylate 9 (30.0 g, 122.3 mmol) was covered with 20% aq HCl (400 mL) and the mixture was refluxed with stirring for 8 h. The solid phase gradually dissolved and a clear solutionformed. The mixture was allowed to equilibrate to r.t. and leftovernight without stirring. The precipitate was filtered off and the filtrate was extracted with CH2Cl2 (5 × 60 mL). The aqueous phase was evaporated to dryness, the residue was heated under vacuum (60 °C/0.4 mbar) for 90 min, triturated (i-PrOH, 20 mL) and filtered to give pure product as white crystals that required no further purification; yield: 18.1 g (116.2 mmol, 95%); mp 221-222 °C (dec.) [Lit.13,15 mp 220-222 °C (H2O-acetone)]. IR (KBr): 3402, 2980, 2923, 1733, 1531, 1189, 834, 551 cm-1. 1 NMR (400 MHz, DMSO-d6): δ = 1.27 (s, 2 H, cyclopropyl), 1.37 (s, 2H, cyclopropyl), 8.90 (br s, 3 H, NH3). 13C NMR (100 MHz, DMSO-d6): δ = 13.1, 33.7, 171.5. MS (APCI): m/z = 102.0 [M + H]+.

References:

Dobrydnev, Alexey V.;Popova, Maria V.;Saffon-Merceron, Nathalie;Listunov, Dymytrii;Volovenko, Yulian M. [Synthesis,2015,vol. 47,# 17,art. no. SS-2015-T0209-ST,p. 2523 - 2528]

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