(4E)-N-Methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-imine → 6-Methylchroman-4-amine

HRID 1662140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662140
CO[N:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[CH:12]=2)[O:7][CH2:6][CH2:5]1>N.CO.[Ni]>[CH3:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[O:7][CH2:6][CH2:5][CH:4]2[NH2:3]

Komponenten

5

Edukt 1

HCID 86605441(4E)-N-Methoxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-imine

Produkt 1

HCID 162444176-Methylchroman-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of Example 7A (4.24 g) in 20% ammonia in methanol (50 mL) was treated with Raney Nickel, 40 g, under hydrogen (60 psi) for 4 hours at ambient temperature. The mixture was filtered, and the solvent was evaporated under reduced pressure. The residue dissolved in diethyl ether which was washed sequentially with water and saturated aqueous sodium bicarbonate, dried with magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound. H NMR (300 MHz, CDCl3) δ ppm 1.78-1.88 (m, 1H), 2.10-2.21 (m, 1H), 2.27 (s, 3H), 4.01 (m, 1H), 4.22 (m, 2H), 6.71 (d, J=8.5 Hz, 1H), 6.95 (d, J=8.5 Hz, 1H), 7.11 (s, 1H). MS (DCI) m/z 164 (M+H)+.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue dissolved in diethyl ether which
  4. washwas washed sequentially with water and saturated aqueous sodium bicarbonate
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-efa59bd1824f4562a29c4473fedaa3ae
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030504B2

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