Malonic Acid → 3-Amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid

HRID 1941240Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=O)[CH3:2].[C:14]([O-:17])(=[O:16])[CH3:15].[NH4+:18].C(O)(=O)CC(O)=O>C(O)C>[NH2:18][CH:7]([C:6]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[CH2:15][C:14]([OH:17])=[O:16]

Participants

Conditions

Temperature: 45 °C

Procedure

A stirred mixture of 3-ethoxy-4-methoxybenzaldehyde (119.5 grams, 664 mmol) and ammonium acetate (148.3 grams, 1.92 mol) in ethanol (300 mL, 95%) was heated at 45° C. To the mixture was added malonic acid (69 grams, 664 mmol), followed by ethanol (100 mL, 95%). The mixture was refluxed for 18 hours. The mixture was cooled to room temperature and was stirred for 2 hours. The suspension was filtered and the solid was washed with cold ethanol (5×50 mL) to give 3-amino-3-(3'-ethoxy-4'-methoxyphenyl)propionic acid as a white solid, which was dried in a vacuum oven overnight, (94.75 grams, 60% yield): mp, 224.0°-225.5° C.; 1H NMR (D2O/NaOD)δ1.41 (t, J=7 Hz, 3H, CH3), 2.52-2.56 (m, 2H, CH2), 3.83 (s, 3H, CH2), 4.14 (q, J=7 Hz, 2H, CH2), 4.19 (t, J=7 Hz, 1H, NCH), 6.98-7.04 (m, 3H, Ar); 13C NMR (D2O/NaOD)δ16.75, 49.81, 55.45, 58.46, 67.63, 114.17, 114.71, 121.76, 140.69, 149.91, 150.09, 182.97; Anal. Calcd for C12H17NO4 : C, 60.24; H, 7.16; N, 5.85. Found: C, 60.21; H, 7.12;N, 5.88.

Workup

temperatureThe mixture was refluxed for 18 hours
temperatureThe mixture was cooled to room temperature
filtrationThe suspension was filtered
washthe solid was washed with cold ethanol (5×50 mL)

Sources & evidence

ORD record: ord-57bcb241f5cd4543be3d5a45c88cefb3
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05703098

Reaction notes

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