Diethyl (ethoxymethylene)malonate → Diethyl 2-(4-benzyloxy-3-methoxyanilino)methylenemalonate

HRID 1822828Notes

Reaction equation

HRID 1822828 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:21]=[C:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>C(O)C>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 272264-(Benzyloxy)-3-methoxyaniline

Product 1

HCID 22170195Diethyl 2-(4-benzyloxy-3-methoxyanilino)methylenemalonateYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(Benzyloxy)-3-methoxyaniline (9.3 g, 40 mmol) and diethyl ethoxymethylenemalonate (9.65 g, 45 mmol) were heated at 120° C. for 1–1.5 h, the ethanol produced was removed under reduced pressure, affording 16 g (100% yield) of the title compound.

Workup

  1. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-88480e258e404b8b8deeef16f3ec8dde
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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