2-Amino-p-cymene → HCID 71238849, Verbindung

HRID 80830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80830
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:17]=[C:16]([O:18][CH3:19])[C:12]([C:13]([O-])=[O:14])=[C:11]([CH:20]=[CH2:21])[N:10]=1.[CH:22]([C:25]1[CH:26]=[CH:27][C:28]([CH3:32])=[C:29]([CH:31]=1)[NH2:30])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:17]=[C:16]([O:18][CH3:19])[C:12]2[C:13](=[O:14])[N:30]([C:29]3[CH:31]=[C:25]([CH:22]([CH3:23])[CH3:24])[CH:26]=[CH:27][C:28]=3[CH3:32])[CH2:21][CH2:20][C:11]=2[N:10]=1

Komponenten

5

Edukt 2

HCID 1374142-Amino-p-cymeneHCID 866902806-(2,6-Dimethylphenyl)-4-methoxy-2-vinylnicotinate

Produkt 1

HCID 71238849HCID 71238849, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 6-(2,6-dimethylphenyl)-4-methoxy-2-vinylnicotinate (1.77 g, 5.95 mmol) and 5-isopropyl-2-methylaniline (4.44 g, 29.8 mmol) in toluene (26.5 mL) and acetic acid (13.2 mL) was heated to 110° C. and stirred at that temperature. After 12 h, the reaction mixture was removed from the heat and concentrated on the rotovap to remove the bulk of the solvent. The residue was partitioned between EtOAc and aqueous 1 N sodium hydroxide solution with added brine. The layers were separated and the aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, then dried over sodium sulfate, filtered, and concentrated. The residue was purified by FCC (0-15% EtOAc/DCM) to provide 2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-4-methoxy-7,8-dihydro-1,6-naphthyridin-5(6H)-one. The product contained some 5-isopropyl-2-methylaniline and was used in the next step without further purification. MS (ESI+) m/z 415.2 (M+H)+.

Aufarbeitung

  1. customthe reaction mixture was removed from the
  2. temperatureheat
  3. concentrationconcentrated on the rotovap
  4. customto remove the bulk of the solvent
  5. customThe residue was partitioned between EtOAc and aqueous 1 N sodium hydroxide solution with added brine
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with EtOAc (3×)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by FCC (0-15% EtOAc/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-843bf64278b74feb9a10db6d0def6ae9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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