Diethyl (ethoxymethylene)malonate → HCID 178469633, compound

HRID 495475Notes

Reaction equation

HRID 495475 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].CC[O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:7]([C:13]([OH:12])=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:20]=[N:6]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 108243-Methoxyaniline

Product 1

HCID 178469633HCID 178469633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of m-methoxyaniline (35 g, 0.28 mol) and diethyl ethoxymethylene malonate (74 g, 0.34 mol) was stirred 2 h at 110° C. under reduce pressure. The mixture was heated at 240° C. under reduced pressure for an additional 2 h. The resulting solid was suspended in CH2Cl2, filtered off and washed with CH2Cl2 to yield 7-methoxy-4-hydroxy-3-ethoxycarbonylquinoline as a white solid.

Workup

  1. temperatureThe mixture was heated at 240° C. under reduced pressure for an additional 2 h
  2. filtrationfiltered off
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-2d618308b676486b94a71cbe1e02ea7c
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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