Acetic Acid → 7-methoxy-2-methyl-1H-indole

HRID 480573

Reaktionsgleichung

Reaktionsgleichung von HRID 480573
[N+]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:12]=[C:13]([N+:15]([O-])=O)[CH3:14])([O-])=O.CCOC(C)=O.C(O)(=O)C>[Pd].CCO>[CH3:14][C:13]1[NH:15][C:4]2[C:5]([CH:12]=1)=[CH:6][CH:7]=[CH:8][C:9]=2[O:10][CH3:11]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 534141941-Methoxy-2-nitro-3-(2-nitroprop-1-en-1-yl)benzene

Produkt 1

HCID 3266147-methoxy-2-methyl-1H-indoleAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 2 L hydrogenation flask were added 1-(2-Nitro-3-methoxyphenyl)-2-nitropropene (44 g, 0.1850 mol), 10% Pd/C (4.4 g, 50% water wet), EtOAc (600 mL), acetic acid (90 mL) and absolute EtOH (75 mL). The reaction mixture was hydrogenated at <60 psi for 3 h and then filtered. The cake was washed with EtOAc (3×100 mL). The filterate was concentrated to remove EtOAc and EtOH. DI water (200 mL) was then added slowly. The resulting slurry was stirred for 0.5 h at RT and filtered. The cake was washed with 1:2 HOAc/H2O (2×30 mL) 1:4 HOAc/H2O (50 mL), water (2×80 mL) and suction dried for 18 h to give 2-methyl-7-methoxyindole (8.3 g, 62% yield). 1H NMR (CDCl3) δ2.42 (s, 3H), 3.94 (s, 3H), 6.18 (pseudo t, J=1.1 Hz, 1H), 6.57 (d, J=7.7 Hz, 1H), 6.97 (pseudo t, J=7.7 Hz, 1H), 7.12 (d, J=7.7 Hz, 1H), 8.10 (s, 1H).

Aufarbeitung

  1. filtrationfiltered
  2. washThe cake was washed with EtOAc (3×100 mL)
  3. concentrationThe filterate was concentrated
  4. customto remove EtOAc and EtOH
  5. additionDI water (200 mL) was then added slowly
  6. filtrationfiltered
  7. washThe cake was washed with 1:2 HOAc/H2O (2×30 mL) 1:4 HOAc/H2O (50 mL), water (2×80 mL) and suction
  8. customdried for 18 h

Quellen und Nachweise

ORD-Eintrag
ord-fc95bfbe04b24d1e983226668d6a88c5
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653304B2

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