Dimethyl 3-oxoglutarate → Methyl 3-[7-(diethylamino)-2-oxo-2h-chromen-3-yl]-3-oxopropanoate

HRID 25875

Reaction equation

HRID 25875 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:10][CH:11]=1)[CH:8]=O)[CH3:2].[CH3:15][O:16][C:17]([CH2:19][C:20]([CH2:22][C:23](OC)=[O:24])=[O:21])=[O:18]>>[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:5]=[C:6]2[C:7]([CH:8]=[C:22]([C:20]([CH2:19][C:17]([O:16][CH3:15])=[O:18])=[O:21])[C:23](=[O:24])[O:12]2)=[CH:10][CH:11]=1)[CH3:2]

Participants

3

Reactant 2

HCID 74591Dimethyl 3-oxoglutarateHCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

Product 1

HCID 3326307Methyl 3-[7-(diethylamino)-2-oxo-2h-chromen-3-yl]-3-oxopropanoate

Procedure

A solution of 1.93 g 4-diethylaminosalicylaldehyde, 1.80 g. dimethyl 1,3-acetone dicarboxylate in 10 ml. alcohol containing 10 drops piperidine was heated under reflux on a steam bath for 2 hours. After chilling in the freezer, the product was collected and recrystallized from a mixture of alcohol and acetonitrile. Yield 2.6 g (82%).

Workup

  1. temperatureunder reflux on a steam bath for 2 hours
  2. temperatureAfter chilling in the freezer
  3. customthe product was collected
  4. customrecrystallized from a mixture of alcohol and acetonitrile

Sources & evidence

ORD record
ord-9bb7a49ccb15458eb06d178ed62e3219
Source dataset
uspto-grants-1979_04
Patent number
US04147552

Linked notes

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