Potassium Carbonate → Ethyl 7-(4-carbamoyl-2-nitrophenoxy)-6-chlorochroman-4-carboxylate

HRID 1626408

Reaktionsgleichung

Reaktionsgleichung von HRID 1626408
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][CH:5]2[C:13]([O:15][CH2:16][CH3:17])=[O:14].Cl[C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][C:20]=1[N+:28]([O-:30])=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:23]([C:22]1[CH:26]=[CH:27][C:19]([O:12][C:11]2[CH:10]=[C:9]3[C:4]([CH:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][CH2:7][O:8]3)=[CH:3][C:2]=2[Cl:1])=[C:20]([N+:28]([O-:30])=[O:29])[CH:21]=1)(=[O:24])[NH2:25]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 279424-Chloro-3-nitrobenzamideHCID 53393319Ethyl-6-chloro-7-hydroxy-3,4-dihydro-2H-chromene-4-carboxylate

Produkt 1

HCID 67287592Ethyl 7-(4-carbamoyl-2-nitrophenoxy)-6-chlorochroman-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of ethyl 6-chloro-7-hydroxychroman-4-carboxylate (6.40 g, 24.9 mmol) and 4-chloro-3-nitrobenzamide in N,N′-dimethylformamide (75 mL) at ambient temperature was added potassium carbonate (8.61 g, 62.3 mmol). An argon balloon with purge valve was attached, and the stirred mixture was evacuated and purged 5 times with argon. The mixture was stirred in an oil bath at 90° C. under argon. After 15 hours the reaction mixture was cooled to ambient temperature, then poured into a reparatory funnel containing water (1000 mL) and the extracted with ether (2×1000 mL). The organic layers were combined and dried over sodium sulfate, then evaporated to give 10.5 g of brown semi-solid. The crude material was purified by silica gel column chromatography, eluting with 99/1 chloroform/methanol followed by 98/2 chloroform/methanol to provide the desired product (7.74 g, 74%).

Aufarbeitung

  1. customAn argon balloon with purge valve
  2. customthe stirred mixture was evacuated
  3. custompurged 5 times with argon
  4. temperatureAfter 15 hours the reaction mixture was cooled to ambient temperature
  5. additionpoured into a reparatory funnel
  6. additioncontaining water (1000 mL)
  7. extractionthe extracted with ether (2×1000 mL)
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c1b39eb3f70f440594d30dc1127ef034
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785445B2

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