Acetic Acid → Methyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

HRID 557403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557403
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2.[C:16]([CH:18]=[C:19]([O-])[CH3:20])#[N:17].[Na+].[NH2:23]/[C:24](/[CH3:30])=[CH:25]\[C:26]([O:28][CH3:29])=[O:27].C(O)(=O)C>CC(O)C>[C:16]([C:18]1[CH:12]([C:9]2[CH:10]=[CH:11][C:2]([F:1])=[C:3]3[C:8]=2[O:7][C:6]([CH3:14])=[CH:5][C:4]3=[O:15])[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([CH3:30])[NH:23][C:19]=1[CH3:20])#[N:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 643918Methyl 3-aminocrotonateHCID 574388885-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Produkt 1

HCID 15979219Methyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 100 mg (0.49 mmol) of 5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 50.96 mg (0.49 mmol) of sodium 1-cyanoprop-1-en-2-olate, 55.84 mg (0.49 mmol) of methyl 3-aminocrotonate and 0.04 ml (0.73 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is taken up in dichloromethane and washed with water. The organic phase is dried over sodium sulfate and concentrated. The resulting residue is crystallized from diethyl ether. The beige-colored crystals are filtered off with suction and dried at 40° C. in a vacuum drying oven. 128.3 mg (71.8% of theory) of the title compound are obtained.

Aufarbeitung

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. washwashed with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is crystallized from diethyl ether
  8. filtrationThe beige-colored crystals are filtered off with suction
  9. customdried at 40° C. in a vacuum
  10. customdrying oven

Quellen und Nachweise

ORD-Eintrag
ord-45f146c5cbcc426fa4b5f387e35ae19d
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058447B2

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