Hydrazine hydrate (1:1) → 1-(6-Amino-5-methoxy-2,3-dihydro-1H-indol-1-yl)-2-(dimethylamino)ethan-1-one

HRID 1014247

Reaktionsgleichung

Reaktionsgleichung von HRID 1014247
[CH3:1][N:2]([CH3:20])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5].O.NN>CO.[Fe](Cl)(Cl)Cl>[CH3:20][N:2]([CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([NH2:15])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:1]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 594418292-(Dimethylamino)-1-(5-methoxy-6-nitroindolin-1-yl)ethanone

Produkt 1

HCID 534147641-(6-Amino-5-methoxy-2,3-dihydro-1H-indol-1-yl)-2-(dimethylamino)ethan-1-oneAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A suspension of N,N-dimethyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1 H-indol-1-yl]-2-oxoethanamine (26.6 g, 95 mmol), iron(III)chloride (3.09 g, 19.05 mmol), activated carbon (25 g, 95 mmol), and hydrazine hydrate (37.4 mL, 762 mmol) in methanol (500 mL) was warmed to 65° C. and maintained overnight. The reaction was filtered through celite while still warm and all methanol was removed under reduced pressure. The solids were partitioned between ethyl acetate (ca 1 L) and saturated sodium chloride (ca 1 L) and the aqueous layer was washed twice with ethyl acetate (ca 500 mL). The combined organic layers were dried over sodium sulfate, taken to a residue under reduced pressure, and the derived solids triturated with hexanes/diether ether and filtered to afford 1-[(dimethylamino)acetyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (16.46 g, 69.3% yield) as an off-white solid: NMR: 1H NMR (400 MHz, DMSO-d6) δ ppm 2.23 (s, 6 H), 2.95 (t, J=8.25 Hz, 2 H), 3.11 (s, 2H), 3.69 (s, 3 H), 4.07 (s, 2 H), 4.61 (s, 2 H), 6.68 (s, 1 H), 7.53 (s, 1 H).

Aufarbeitung

  1. temperaturemaintained overnight
  2. filtrationThe reaction was filtered through celite
  3. temperaturewhile still warm
  4. customall methanol was removed under reduced pressure
  5. customThe solids were partitioned between ethyl acetate (ca 1 L) and saturated sodium chloride (ca 1 L)
  6. washthe aqueous layer was washed twice with ethyl acetate (ca 500 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe derived solids triturated with hexanes/diether ether
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-e52e6f4cd60c4ad8b27a9d5c6ddaf426
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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