3-(dimethylamino)-N-(3-nitrophenyl)propanamide → N-(3-Aminophenyl)-3-(dimethylamino)propanamide

HRID 716856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716856
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:6]>[Pd].C(OCC)(=O)C>[NH2:14][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][CH2:3][N:2]([CH3:17])[CH3:1])[CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 1

HCID 866899623-(dimethylamino)-N-(3-nitrophenyl)propanamide

Produkt 1

HCID 16781477N-(3-Aminophenyl)-3-(dimethylamino)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

10% Palladium on charcoal (1.0 g) was suspended in a solution of 3-(dimethylamino)-N-(3-nitrophenyl)propanamide (4.7 g, 20 mmol) in ethyl acetate. The mixture was hydrogenated at 35 psi overnight. The reaction mixture was filtered through a pad of Celite. The filter cake was washed successively with ethyl acetate and methanol. The combined filtrate and washings were evaporated in vacuo to dryness to give N-(3-aminophenyl)-3-(dimethylamino)propanamide as brown gum, 3.9 g (94%). 1H NMR (DMSO-d6) δ: 2.16 (6H, s, CH3), 2.36 (2H, t, J=6.8 Hz, CH2), 3.40 (2H, t, J=6.8 Hz, CH2), 5.20 (2H, brs, NH2), 6.66 (1H, d, J=7.8 Hz, Ar—H), 6.91 (1H, d, J=7.7 Hz, Ar—H), 7.04 (1H, s, Ar—H), 7.15 (1H, t, J=7.4 Hz, Ar—H), 9.05-9.08 (1H, brs, NH).

Aufarbeitung

  1. customwas hydrogenated at 35 psi overnight
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washThe filter cake was washed successively with ethyl acetate and methanol
  4. customThe combined filtrate and washings were evaporated in vacuo to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8c2b3da08af64b6eb68b8cafbf7fab93
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193687B2

Notizen zur Reaktion

Wird geladen…