Diethyl (ethoxymethylene)malonate → Diethyl (2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydro-1-quinolinyl)methylenemalonate

HRID 1199126Notes

Reaction equation

HRID 1199126 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:13])[C:8]=2[CH3:12])[NH:3]1.C(O[CH:17]=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:13])[C:8]=2[CH3:12])[N:3]1[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 136692466-Fluoro-2,5-dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 13669249Diethyl (2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydro-1-quinolinyl)methylenemalonate

Conditions

Temperature
110 °C

Procedure

3350 g (18.7 mole) of 2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydroquinoline and 4445.7 g (20.6 mole) of diethyl ethoxymethylenemalonate were combined and heated to 110° C. The ethanol was removed by atmospheric distillation initially and then through vacuum distillation when the reaction temperature reached 150° C. The resulting material, diethyl (2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydro-1-quinolinyl)methylenemalonate, was used directly in the next step.

Workup

  1. customThe ethanol was removed by atmospheric distillation initially
  2. distillationthrough vacuum distillation when the reaction temperature
  3. customreached 150° C

Sources & evidence

ORD record
ord-2950643272044237a9a4b0526028e125
Source dataset
uspto-grants-1990_02
Patent number
US04898945

Reaction notes

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