Diethyl (ethoxymethylene)malonate → HCID 135819170, compound

HRID 513919Notes

Reaction equation

HRID 513919 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]=[C:11]([C:17](OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:7][CH:8]=1.C(OC=C(C(OCC)=O)C(OCC)=O)C.COC1C=CC=C(N)C=1>>[OH:2][C:3]1[CH:4]=[C:5]2[C:6]([CH:17]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=[N:9]2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 108243-MethoxyanilineHCID 3904966Diethyl 2-(((3-methoxyphenyl)amino)methylene)malonate

Product 1

HCID 135819170HCID 135819170, compoundYield 99%

Conditions

Temperature
125 °C

Procedure

Diethyl 2-(((3-methoxyphenyl)amino)methylene)malonate. Diethyl ethoxymethylenemalonate (5.00 g, 40.6 mmol) and m-anisidine (8.13 mL, 40.6 mmol) were mixed and heated at 125° C. for 3 h. After cooling to ambient temperature, residual solvent was removed under reduced pressure and dried under high vacuum to afford the title compound as a yellow oil (11.81 g, 99%). 1H NMR (400 MHz, CDCl3) δ 11.57 (d, J=13.7 Hz, 1H), 9.11 (d, J=13.7 Hz, 1H), 7.90-7.83 (m, 1H), 7.31 (ddd, J=15.5, 8.2, 2.2 Hz, 2H), 7.25 (d, J=2.3 Hz, 1H), 4.90 (q, J=7.0 Hz, 2H), 4.84 (q, J=7.3 Hz, 2H), 4.42 (s, 3H), 1.98 (t, J=7.0 Hz, 3H), 1.92 (t, J=7.0 Hz, 3H). [M+H]=294.3.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customresidual solvent was removed under reduced pressure
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-d04d389b96bf4c3fb477d42d56d1ebdb
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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