Aniline → 2-Phenylaminomethylene-malonic acid diethyl ester

HRID 1915214Notes

Reaction equation

HRID 1915214 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])C>>[CH2:16]([O:15][C:13](=[O:14])[C:12](=[CH:11][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:17]

Participants

3

Reactant 2

HCID 6115AnilineHCID 6871Diethyl (ethoxymethylene)malonate

Product 1

HCID 2643272-Phenylaminomethylene-malonic acid diethyl ester

Conditions

Temperature
145 °C

Procedure

A mixture of aniline (25.6 g, 0.28 mol) and diethyl 2-(ethoxymethylene)malonate (62.4 g, 0.29 mol) was heated at 140-150° C. for 2 h. The mixture was cooled to room temperature and dried under reduced pressure to afford 2-phenylaminomethylene-malonic acid diethyl ester as a solid, which was used in the next step without further purification. 1H NMR (d-DMSO) δ 11.00 (d, 1H), 8.54 (d, J=13.6 Hz, 1H), 7.36-7.39 (m, 2H), 7.13-7.17 (m, 3H), 4.17-4.33 (m, 4H), 1.18-1.40 (m, 6H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-0327d72608174a2fb042953a7ef88ddd
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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