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

HRID 929536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929536
[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-ca2cdb2e8f284da8bb919cc0c9e5e1ce
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296701B2

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