Hydrazine → 2-(2-Methoxyphenyl)propan-1-amine

HRID 2207707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207707
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH3:22])[CH2:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O.NN>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH3:22])[CH2:10][NH2:11]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 866996512-(2-(2-Methoxyphenyl)propyl)isoindoline-1,3-dione

Produkt 1

HCID 4080602-(2-Methoxyphenyl)propan-1-amineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

As shown in step 4-iv of Scheme 4, to a stirred solution of 2-(2-(2-methoxyphenyl)propyl)isoindoline-1,3-dione (363 mg, 1.23 mmol) in MeOH (4.0 mL) was added hydrazine (39.4 mg, 38.6 μL, 1.23 mmol) and the reaction was stirred for 18 hours. The precipitate that had formed was filtered, washed with MeOH, and the filtrate concentrated under reduced pressure to give 2-(methoxyphenyl)-1-propanamine as a light yellow oil (Compound 2011, 144 mg, 71% yield): 1H NMR (CDCl3) δ 7.27-7.13 (m, 2H), 6.95 (ddd, J=18.2, 12.3, 4.6 Hz, 2H), 3.84 (s, 3H), 3.39-3.18 (m, 1H), 2.86 (qd, J=12.7, 6.8 Hz, 2H), 1.44 (s, 2H), 1.24 (d, J=7.0 Hz, 3H).

Aufarbeitung

  1. customThe precipitate that had formed
  2. filtrationwas filtered
  3. washwashed with MeOH
  4. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d51f223e0a4c42dc9783b9352bf5aad4
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376448B2

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