N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide → 4-(7-methoxy-2-methyl-3H-benzo[d]imidazol-5-yl)morpholine

HRID 1188778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188778
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[C:5]([N+:15]([O-])=O)[C:4]=1[NH:18][C:19](=O)[CH3:20]>CC(O)=O.[Fe]>[CH3:1][O:2][C:3]1[C:4]2[N:18]=[C:19]([CH3:20])[NH:15][C:5]=2[CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1

Komponenten

4

Edukt 1

HCID 66977019N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide

Produkt 1

HCID 669771484-(7-methoxy-2-methyl-3H-benzo[d]imidazol-5-yl)morpholineAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a refluxing solution of combined batches of N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide (2.06 g) in HOAc (60 mL) was added iron powder (1.18 g) and the mixture was stirred at reflux temperature overnight. It was cooled to room temperature and filtered. The filtrate was concentrated in-vacuo and the residue was washed with EtOAc:petroleum ether=1:1 to afford crude product as a solid (1.73 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.56 (s, 3H), 3.12 (t, 4H, J=4.8 Hz), 3.88 (t, 4H, J=4.8 Hz), 3.94 (s, 3H), 6.39 (s, 1H), 6.62 (s, 1H); LC-MS: m/e=248 [M+1]+

Aufarbeitung

  1. temperatureat reflux temperature overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in-vacuo
  4. washthe residue was washed with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-0cc34f4420f54b1e8b3443c73cb0afc5
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674090B2

Notizen zur Reaktion

Wird geladen…