Diethyl (ethoxymethylene)malonate → Diethyl 2-[(4-fluoroanilino)methylene]malonate

HRID 1944547Notes

Reaction equation

HRID 1944547 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[CH:12][NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 97314-Fluoroaniline

Product 1

HCID 595792Diethyl 2-[(4-fluoroanilino)methylene]malonate

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoro-phenylamine (5.1 mL, 54.4 mmol) and diethyl ethoxymethylenemalonate (10 mL, 49.5 mmol) was heated at 100° C. for 4 hours, an oil which solidified on cooling. The solid was triturated in heptane, collected by filtration and washed with heptane, to give the product as a colorless solid, 10.5 g (75%). MS: m/z 282.1 (MH+).

Workup

  1. temperatureon cooling
  2. customThe solid was triturated in heptane
  3. filtrationcollected by filtration
  4. washwashed with heptane

Sources & evidence

ORD record
ord-3b66e682b83f455f8328c78b7d89b47d
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

Loading…