Malonic Acid → 3-[3-(Acetylamino)-4-methylphenyl]-2-propenoic acid

HRID 651604Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[CH3:13])[CH:8]=O)(=[O:3])[CH3:2].N1CCCCC1.C(O)(=O)[CH2:21][C:22]([OH:24])=[O:23].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:21][C:22]([OH:24])=[O:23])[CH:10]=[CH:11][C:12]=1[CH3:13])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-acetamido-4-methylbenzaldehyde (14 g, 79 mmol) in pyridine (210 mL) is added piperidine (3.9 mL, 39.4 mmol) and malonic acid (15.26 g, 146.6 mmol). The mixture is heated to 100° C. for 4 hours, then stirred at room temperature overnight. The solution is concentrated in vacuo, then diluted with water. Cold 1 N HCl is added to the slurry until pH is ca. 4. The solid product (16.178 g, 73.8 mmol) is collected and washed generously with water. The title compound (16.178 g, 73.8 mmol) is then dried over P2O5 under vacuum overnight to yield a white solid.

Workup

concentrationThe solution is concentrated in vacuo
additiondiluted with water
additionCold 1 N HCl is added to the slurry until pH is ca. 4
washwashed generously with water

Sources & evidence

ORD record: ord-5c2ced6830f74bdf86360dab41df92c4
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06281227B1

Reaction notes

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