Dimethylformamide → 7-(Diethylamino)-2-oxo-2H-chromene-3-carbaldehyde

HRID 328753Notes

Reaction equation

HRID 328753 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:8]([CH2:20][CH3:21])[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[O:16]2)=[CH:11][CH:10]=1)[CH3:7].CN(C)[CH:24]=[O:25]>>[CH2:20]([N:8]([CH2:6][CH3:7])[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([CH:24]=[O:25])[C:15](=[O:19])[O:16]2)=[CH:11][CH:10]=1)[CH3:21]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 885987-Diethylaminocoumarin

Product 1

HCID 1431917-(Diethylamino)-2-oxo-2H-chromene-3-carbaldehydeYield 86.5%

Conditions

Temperature
50 °C

Procedure

20 g of dimethylformamide are added dropwise to 40 g of phosphorus oxychloride at 20°-50° C. The mixture is stirred for 45 minutes at 50° C whilst excluding moisture. A suspension of 42 g of 7-diethylamino-coumarin in 50 g of dimethylformamide is then added, the mixture is warmed to 60° C for 2 hours and poured out onto 400 g of ice water, and the whole is stirred for 2 hours. The crystalline precipitate is filtered off, thoroughly washed with water and dried in vacuo at 70° C. 41 g of 7-diethylamino-coumarin-3-aldehyde are obtained.

Workup

  1. additionis then added
  2. temperaturethe mixture is warmed to 60° C for 2 hours
  3. stirringthe whole is stirred for 2 hours
  4. filtrationThe crystalline precipitate is filtered off
  5. washthoroughly washed with water
  6. customdried in vacuo at 70° C

Sources & evidence

ORD record
ord-94542b5be3bb43b3af987cbb366032a5
Source dataset
uspto-grants-1977_04
Patent number
US04018796

Reaction notes

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